{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,1]],"date-time":"2026-02-01T12:15:29Z","timestamp":1769948129426,"version":"3.49.0"},"reference-count":115,"publisher":"MDPI AG","issue":"6","license":[{"start":{"date-parts":[[2017,6,15]],"date-time":"2017-06-15T00:00:00Z","timestamp":1497484800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT)","award":["PTDC\/QEQ-QOR\/6160\/2014"],"award-info":[{"award-number":["PTDC\/QEQ-QOR\/6160\/2014"]}]},{"name":"Funda\u00e7\u00e3o para a Ci\u00eancia e a Tecnologia (FCT)","award":["FCT UID\/QUI\/00062\/2013"],"award-info":[{"award-number":["FCT UID\/QUI\/00062\/2013"]}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>This review covers the synthesis of coumarin\u2013porphyrin, coumarin\u2013phthalocyanine and coumarin\u2013corrole conjugates and their potential applications. While coumarin\u2013phthalocyanine conjugates were obtained almost exclusively by tetramerization of coumarin-functionalized phthalonitriles, coumarin\u2013porphyrin and coumarin\u2013corrole conjugates were prepared by complementary approaches: (a) direct synthesis of the tetrapyrrolic macrocycle using formylcoumarins and pyrrole or (b) by functionalization of the tetrapyrrolic macrocycle. In the last approach a range of reaction types were used, namely 1,3-dipolar cycloadditions, hetero-Diels\u2013Alder, Sonogashira, alkylation or acylation reactions. This is clearly a more versatile approach, leading to a larger diversity of conjugates and allowing the access to conjugates bearing one to up to 16 coumarin units.<\/jats:p>","DOI":"10.3390\/molecules22060994","type":"journal-article","created":{"date-parts":[[2017,6,15]],"date-time":"2017-06-15T10:07:33Z","timestamp":1497521253000},"page":"994","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":24,"title":["Coumarin\u2013Tetrapyrrolic Macrocycle Conjugates: Synthesis and Applications"],"prefix":"10.3390","volume":"22","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2306-638X","authenticated-orcid":false,"given":"Ana","family":"Cerqueira","sequence":"first","affiliation":[{"name":"Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"given":"V\u00edtor","family":"Almod\u00f4var","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-7953-8166","authenticated-orcid":false,"given":"Maria","family":"Neves","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-4331-714X","authenticated-orcid":false,"given":"Augusto","family":"Tom\u00e9","sequence":"additional","affiliation":[{"name":"Department of Chemistry and QOPNA, University of Aveiro, 3810-193 Aveiro, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2017,6,15]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"4960","DOI":"10.1021\/cr400265z","article-title":"Chromone: A valid scaffold in medicinal chemistry","volume":"114","author":"Gaspar","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"6400","DOI":"10.1021\/jm0580149","article-title":"Synthesis and antiinflammatory activity of coumarin derivatives","volume":"48","author":"Kontogiorgis","year":"2005","journal-title":"J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1016\/S0031-9422(02)00023-7","article-title":"Coumarins and \u03b3-pyrone derivatives from Prangos pabularia: Antibacterial activity and inhibition of cytokine release","volume":"59","author":"Tada","year":"2002","journal-title":"Phytochemistry"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"1394","DOI":"10.3390\/molecules18021394","article-title":"Synthesis and structure-activity relationships of novel amino\/nitro substituted 3-arylcoumarins as antibacterial agents","volume":"18","author":"Matos","year":"2013","journal-title":"Molecules"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.bioorg.2014.07.008","article-title":"Novel furocoumarins as potential HIV-1 integrase inhibitors","volume":"57","author":"Olomola","year":"2014","journal-title":"Bioorg. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"236","DOI":"10.1016\/j.ejmech.2016.07.056","article-title":"Therapeutic potential of coumarins as antiviral agents","volume":"123","author":"Hassan","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2664","DOI":"10.2174\/092986708786242877","article-title":"A review of coumarin derivatives in pharmacotherapy of breast cancer","volume":"15","author":"Musa","year":"2008","journal-title":"Curr. Med. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"225","DOI":"10.1016\/j.ejmech.2013.12.061","article-title":"Synthesis, structure\u2013activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and antimycobacterial agentes","volume":"74","author":"Basanagouda","year":"2014","journal-title":"Eur. J. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"1032","DOI":"10.2174\/1871520615666150101125503","article-title":"Coumarin: A promising scaffold for anticancer agents","volume":"15","author":"Kaur","year":"2015","journal-title":"Anti-Cancer Agents Med. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5288","DOI":"10.1021\/jm400025g","article-title":"Synthesis and in vitro photocytotoxicity of coumarin derivatives for one- and two-photon excited photodynamic therapy","volume":"56","author":"Zou","year":"2013","journal-title":"J. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"39","DOI":"10.1111\/j.1478-4408.1987.tb03750.x","article-title":"Fluorescent whitening agents 1973\u20131985","volume":"17","author":"Siegrist","year":"1987","journal-title":"Rev. Prog. Coloration"},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"167","DOI":"10.1016\/j.apsusc.2016.01.110","article-title":"Synthesis of polymeric fluorescent brightener based on coumarin and its performances on paper as light stabilizer, fluorescent brightener and surface sizing agent","volume":"367","author":"Zhang","year":"2016","journal-title":"Appl. Surface Sci."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"14639","DOI":"10.1002\/chem.201302090","article-title":"Multimodal use of new coumarin-based fluorescent chemosensors: Towards highly selective optical sensors for Hg2+ probing","volume":"19","author":"Bazzicalupi","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1301","DOI":"10.1021\/ic9022097","article-title":"Coumarin-based, electron-trapping iridium complexes as highly efficient and stable phosphorescent emitters for organic light-emitting diodes","volume":"49","author":"Ren","year":"2010","journal-title":"Inorg. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"8020","DOI":"10.1166\/jnn.2013.8151","article-title":"New ambipolar blue emitting materials based on amino coumarin derivatives with high efficiency for organic light emitting diodes","volume":"13","author":"Kim","year":"2013","journal-title":"J. Nanosci. Nanotechnol."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"227","DOI":"10.1016\/j.dyepig.2014.06.032","article-title":"N-coumarin derivatives as hole-transporting emitters for high efficiency solution-processed pure green electroluminescent devices","volume":"112","author":"Kotchapradist","year":"2015","journal-title":"Dyes Pigment."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"384","DOI":"10.1002\/cplu.201500572","article-title":"A deep-blue electroluminescent device based on a coumarin derivative","volume":"81","author":"Kumar","year":"2016","journal-title":"ChemPlusChem"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"8239","DOI":"10.1039\/C5CP00193E","article-title":"Coumarin\u2013BODIPY hybrids by heteroatom linkage: Versatile, tunable and photostable dye lasers for UV irradiation","volume":"17","author":"Esnal","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"241","DOI":"10.1002\/adma.200390056","article-title":"Electrically switchable, one-dimensional polymeric resonators from holographic photopolymerization: A new approach for active photonic bandgap materials","volume":"15","author":"Jakubiak","year":"2003","journal-title":"Adv. Mater."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"3059","DOI":"10.1021\/cr030037c","article-title":"Coumarins in polymers: From light harvesting to photo-cross-linkable tissue scaffolds","volume":"104","author":"Trenor","year":"2004","journal-title":"Chem. Rev."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3907","DOI":"10.1021\/jp044851v","article-title":"Photophysical and (photo)electrochemical properties of a coumarin dye","volume":"109","author":"Wang","year":"2005","journal-title":"J. Phys. Chem. B"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"2457","DOI":"10.1002\/chem.201202550","article-title":"Hierarchical self-assembly of a biomimetic light-harvesting antenna based on DNA G-quadruplexes","volume":"19","author":"Oltra","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"2791","DOI":"10.1016\/j.tetlet.2007.01.176","article-title":"Design of molecular two-photon probes for in vivo imaging. 2H-Benzo[h]chromene-2-one derivatives","volume":"48","author":"Kim","year":"2007","journal-title":"Tetrahedron Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"210","DOI":"10.3390\/molecules14010210","article-title":"The use of coumarins as environmentally-sensitive fluorescent probes of heterogeneous inclusion systems","volume":"14","author":"Wagner","year":"2009","journal-title":"Molecules"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"16556","DOI":"10.1002\/chem.201302037","article-title":"4-Trifluoromethyl-substituted coumarins with large stokes shifts: Synthesis, bioconjugates, and their use in super-resolution fluorescence microscopy","volume":"19","author":"Schill","year":"2013","journal-title":"Chem. Eur. J."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"7531","DOI":"10.1002\/anie.201403890","article-title":"Ultrafluorogenic coumarin\u2013tetrazine probes for real-time biological imaging","volume":"53","author":"Meimetis","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"710","DOI":"10.1016\/j.snb.2014.08.006","article-title":"Highly sensitive and selective colorimetric and fluorescent off\u2013on probe for copper(II) based on unique addition reaction and its imaging in living cells","volume":"204","author":"Yanga","year":"2014","journal-title":"Sens. Actuators B"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"667","DOI":"10.1039\/C3CC47323F","article-title":"A coumarin derivative as a fluorogenic glycoproteomic probe for biological imaging","volume":"50","author":"Rong","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4652","DOI":"10.1016\/j.bmcl.2015.08.029","article-title":"Fluorophore-tagged pharmacophores for antitumor cytotoxicity: Modified chiral lipidic dialkynylcarbinols for cell imaging","volume":"25","author":"Listunov","year":"2015","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"042004","DOI":"10.1088\/2050-6120\/3\/4\/042004","article-title":"Fluorescent dyes with large Stokes shifts for super-resolution optical microscopy of biological objects: A review","volume":"3","author":"Sednev","year":"2015","journal-title":"Method. Appl. Fluoresc."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"11653","DOI":"10.1039\/c3cc46498a","article-title":"NIR-fluorescent coumarin-fused BODIPY dyes with large Stokes shifts","volume":"49","author":"Bochkov","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1036","DOI":"10.1039\/B601649A","article-title":"Synthesis and fluorescence properties of [60] and [70]fullerene\u2013coumarin dyads: Efficient dipole\u2013dipole resonance energy transfer from coumarin to fullerene","volume":"30","author":"Brites","year":"2006","journal-title":"New J. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"7445","DOI":"10.1039\/C5OB01005E","article-title":"Exploring carbonic anhydrase inhibition with multimeric coumarins displayed on a fullerene scaffold","volume":"13","author":"Supuran","year":"2015","journal-title":"Org. Biomol. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"158","DOI":"10.1016\/j.dyepig.2014.11.005","article-title":"New coumarin\u2013[60]fullerene dyads connected by an alkynyl linkage: Synthesis and fluorescence studies. Evidence for efficient singlet\u2013singlet energy transfer","volume":"114","author":"Nascimento","year":"2015","journal-title":"Dyes Pigment."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"3354","DOI":"10.1039\/b711681k","article-title":"Intramolecular energy transfer in a tetra-coumarin perylene system: Influence of solvent and bridging unit on electronic properties","volume":"5","author":"Hurenkamp","year":"2007","journal-title":"Org. Biomol. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"12944","DOI":"10.1021\/jp075454y","article-title":"Optical energy transport and interactions between the excitations in a coumarin\u2013perylene bisimide dendrimer","volume":"111","author":"Augulis","year":"2007","journal-title":"J. Phys. Chem. A"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"548","DOI":"10.1039\/C4NJ01565G","article-title":"Synthesis and use of \u201dclickable\u201d bay-region tetrasubstituted perylene tetracarboxylic tetraesters and a perylene monoimide diester as energy acceptors","volume":"39","author":"Aydin","year":"2015","journal-title":"New J. Chem."},{"key":"ref_38","first-page":"1841","article-title":"Reaction of \u03b2-vinyl-meso-tetraphenylporphyrin with o-quinone methines","volume":"13","author":"Menezes","year":"2011","journal-title":"Synlett"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"3361","DOI":"10.1016\/j.tet.2013.07.022","article-title":"New coumarin\u2013corrole and \u2013porphyrin conjugate multifunctional probes for anionic or cationic interactions: Synthesis, spectroscopy, and solid supported studies","volume":"70","author":"Santos","year":"2014","journal-title":"Tetrahedron"},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"899","DOI":"10.1016\/0040-4020(73)80035-3","article-title":"Nouvelles voies d\u2019acc\u00e8s aux vinylporphyrins","volume":"29","author":"Callot","year":"1973","journal-title":"Tetrahedron"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1039\/c4pp00359d","article-title":"Untangling interactions of a zinc(II) complex containing a coumarin\u2013porphyrin unit with alkaloids in water solutions: A photophysical study","volume":"14","author":"Santos","year":"2015","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.ijms.2013.03.017","article-title":"Gas phase reactions of \u03b2-substituted hetero-Diels\u2013Alder adducts of meso-tetraphenylporphyrin using tandem mass spectrometry","volume":"343\u2013344","author":"Menezes","year":"2013","journal-title":"Int. J. Mass Spectrom."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"13644","DOI":"10.1002\/chem.201403214","article-title":"Synthesis of new chlorin e6 trimethyl and protoporphyrin IX dimethyl ester derivatives and their photophysical and electrochemical characterizations","volume":"20","author":"Menezes","year":"2014","journal-title":"Chem. Eur. J."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"66192","DOI":"10.1039\/C5RA11156K","article-title":"Ohmic heating assisted synthesis of coumarinyl porphyrin derivatives","volume":"5","author":"Cardoso","year":"2015","journal-title":"RSC Adv."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1419","DOI":"10.1002\/ejoc.200601046","article-title":"Synthesis and versatile reactions of \u03b2-azidotetraarylporphyrins","volume":"2007","author":"Shen","year":"2007","journal-title":"Eur. J. Org. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"68209","DOI":"10.1039\/C5RA13955D","article-title":"Synthesis and photophysical properties of \u03b2-triazole bridged porphyrincoumarin dyads","volume":"5","author":"Singh","year":"2015","journal-title":"RSC Adv."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"545","DOI":"10.1007\/s12039-016-1058-4","article-title":"Synthesis, characterization and photophysical studies of \u03b2-triazolomethyl-bridged porphyrin-benzo-\u03b1-pyrone dyads","volume":"128","author":"Singh","year":"2016","journal-title":"J. Chem. Sci."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"256","DOI":"10.1016\/j.dyepig.2015.05.027","article-title":"meso-Phenyl-triazole bridged porphyrin-coumarin dyads: Synthesis, characterization and photophysical properties","volume":"121","author":"Singh","year":"2015","journal-title":"Dyes Pigment."},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Lin, W., Long, L., Feng, J., Wang, B., and Guo, C. (2007). Synthesis of meso-coumarin-conjugated porphyrins and investigation of their luminescence properties. Eur. J. Org. Chem., 4301\u20134304.","DOI":"10.1002\/ejoc.200700475"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"476","DOI":"10.1021\/jo01288a053","article-title":"A simplified synthesis for meso-tetraphenylporphine","volume":"32","author":"Adler","year":"1967","journal-title":"J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"827","DOI":"10.1021\/jo00381a022","article-title":"Rothemund and Adler-Longo reactions revisited: Synthesis of tetraphenylporphyrins under equilibrium conditions","volume":"52","author":"Lindsey","year":"1987","journal-title":"J. Org. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"821","DOI":"10.1002\/jhet.5570440411","article-title":"Synthesis of meso-tetrakis(4-chlorocoumarin-3-yl)porphyrins","volume":"44","author":"Amaravathi","year":"2007","journal-title":"J. Heterocycl. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"9239","DOI":"10.1021\/ja9922882","article-title":"Porphyrin core star polymers: Synthesis, modification, and implication for site isolation","volume":"121","author":"Hecht","year":"1999","journal-title":"J. Am. Chem. Soc."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"18","DOI":"10.1021\/ja003304u","article-title":"Encapsulation of functional moieties within branched star polymers: Effect of chain length and solvent on site isolation","volume":"123","author":"Hecht","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"4451","DOI":"10.1021\/ol0516824","article-title":"Functionally layered dendrimers: A new building block and its application to the synthesis of multichromophoric light-harvesting systems","volume":"7","author":"Dichtel","year":"2005","journal-title":"Org. Lett."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"975","DOI":"10.1016\/j.dyepig.2011.08.020","article-title":"Non-conjugated dendrimers with a porphyrin core and coumarin chromophores as peripheral units: Synthesis and photophysical properties","volume":"92","author":"Mao","year":"2012","journal-title":"Dyes Pigment."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"1259","DOI":"10.1002\/anie.201611017","article-title":"Not only columns: High hole mobility in a discotic nematic mesophase formed by metal-containing porphyrin-core dendrimers","volume":"56","author":"Marcos","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"7423","DOI":"10.1021\/jo201199k","article-title":"A ratiometric fluorescent probe for thiols based on a tetrakis(4-hydroxyphenyl)porphyrin-coumarin scaffold","volume":"76","author":"Cao","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"1261","DOI":"10.1142\/S1088424608000649","article-title":"Design of metalloporphyrin-based dendritic nanoprobes for two-photon microscopy of oxygen","volume":"12","author":"Lebedev","year":"2008","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1021\/jp030586m","article-title":"Ultrafast energy transport in a first-generation coumarin-tetraphenylporphyrin dendrimer","volume":"108","author":"Hania","year":"2004","journal-title":"J. Phys. Chem. B"},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"65179","DOI":"10.1039\/C6RA13604D","article-title":"Supramolecular liquid crystalline dendrimers with a porphyrin core and functional carboxylic acid dendrons","volume":"6","author":"Bucos","year":"2016","journal-title":"RSC Adv."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"11299","DOI":"10.1021\/jp402265e","article-title":"Artificial photosynthetic reaction center with a coumarin-based antenna system","volume":"117","author":"Garg","year":"2013","journal-title":"J. Phys. Chem. B"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"201","DOI":"10.1007\/s10847-016-0655-7","article-title":"Convenient synthesis of novel unmetalled and metallophthalocyanines bearing coumarin derivatives: Synthesis, characterization, aggregation behaviors and antimicrobial activity","volume":"86","author":"Medyouni","year":"2016","journal-title":"J. Incl. Phenom. Macrocycl. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/j.dyepig.2006.08.037","article-title":"Synthesis and characterization of metal-free and metallo-phthalocyanines with four pendant coumarinthio\/oxy-substituents","volume":"76","author":"Esenpinar","year":"2008","journal-title":"Dyes Pigment."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"17","DOI":"10.1016\/j.molstruc.2013.12.028","article-title":"The synthesis, molecular structure and photophysical properties of 2,9,16,23-tetrakis(7-coumarinoxy-4-methyl)phthalocyanine sensitizer","volume":"1060","author":"Guo","year":"2014","journal-title":"J. Mol. Struct."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"1025","DOI":"10.1071\/CH14502","article-title":"The synthesis, characterisation, photophysical and thermal properties, and photovoltaic performance of 7-coumarinoxy-4-methyltetrasubstituted metallophthalocyanines","volume":"68","author":"Guo","year":"2015","journal-title":"Aust. J. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1039","DOI":"10.1039\/c6pp00172f","article-title":"Metallophthalocyanines as triplet sensitizers for highly efficient photon upconversion based on sensitized triplet\u2013triplet annihilation","volume":"15","author":"Han","year":"2016","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"1829","DOI":"10.1080\/00958972.2015.1023196","article-title":"Synthesis, characterization and electrocatalytic behavior of cobalt and iron phthalocyanines bearing chromone or coumarin substituents","volume":"68","author":"Chohan","year":"2015","journal-title":"J. Coord. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/j.poly.2012.08.080","article-title":"Peripheral octa-substituted metal-free, cobalt(II) and zinc(II) phthalocyanines bearing coumarin and chloro groups: Synthesis, characterization, spectral and electrochemical properties","volume":"48","author":"Altun","year":"2012","journal-title":"Polyhedron"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"540","DOI":"10.1016\/j.dyepig.2012.05.021","article-title":"Novel alpha-7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin substituted metal-free, Co(II) and Zn(II) phthalocyanines: Photochemistry, photophysics, conductance and electrochemistry","volume":"95","author":"Odabas","year":"2012","journal-title":"Dyes Pigment."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"7987","DOI":"10.1039\/c4dt00482e","article-title":"Coumarin-substituted manganese phthalocyanines: Synthesis, characterization, photovoltaic behaviour, spectral and electrochemical properties","volume":"43","author":"Altun","year":"2014","journal-title":"Dalton Trans."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"4341","DOI":"10.1039\/C4DT03301A","article-title":"Gas sensing and electrochemical properties of tetra and octa 2H-chromen-2-one substituted iron(II) phthalocyanines","volume":"44","author":"Altun","year":"2015","journal-title":"Dalton Trans."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"1046","DOI":"10.1142\/S108842461350096X","article-title":"4-Carboxymethyl-8-methyl-7-oxycoumarin substituted zinc, cobalt and indium phthalocyanines: Electrochemical and photochemical properties","volume":"17","author":"Orman","year":"2013","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"3788","DOI":"10.1016\/j.poly.2009.07.060","article-title":"Synthesis, spectroscopy, electrochemistry and in situ spectroelectrochemistry of partly halogenated coumarin phthalonitrile and corresponding metal-free, cobalt and zinc phthalocyanines","volume":"28","author":"Alemdar","year":"2009","journal-title":"Polyhedron"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"1556","DOI":"10.1016\/j.synthmet.2010.05.025","article-title":"Preparation, characterization, electrochemistry and in situ spectroelectrochemistry of novel \u03b1-tetra[7-oxo-3-(2-chloro-4-fluorophenyl)coumarin]-substituted metal-free, cobalt and zinc phthalocyanines","volume":"160","author":"Alemdar","year":"2010","journal-title":"Synth. Met."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1016\/j.jphotochem.2011.07.014","article-title":"Highly soluble 7-oxy-3-(4-methoxyphenyl)coumarin bearing zinc phthalocyanines: Synthesis and investigation of photophysical and photochemical properties","volume":"223","author":"Piskin","year":"2011","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"38","DOI":"10.1016\/j.poly.2012.03.036","article-title":"Synthesis, characterization and electrochemical properties of novel \u03b2 7-oxy-4-(4-methoxyphenyl)-8-methylcoumarin substituted metal-free, Zn(II) and Co(II) phthalocyanines","volume":"39","author":"Odabas","year":"2012","journal-title":"Polyhedron"},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1016\/j.jorganchem.2014.10.014","article-title":"The effects of substituents\u2019 positions and variety of axial groups on the photochemical properties of coumarin substituted indium(III) phthalocyanines","volume":"774","author":"Kaya","year":"2014","journal-title":"J. Organomet. Chem."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"1114","DOI":"10.1142\/S108842461550087X","article-title":"Novel 7-oxy-3-(3\u2032,4\u2032,5\u2032-trimethoxyphenyl)coumarin substituted zinc(II) phthalocyanines: Synthesis, characterization, photophysical and photochemical properties","volume":"19","author":"Kaya","year":"2015","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"163","DOI":"10.1016\/j.jlumin.2015.07.050","article-title":"Photophysical and photochemical properties of novel metallophthalocyanines bearing 7-oxy-3-(m-methoxyphenyl)coumarin groups","volume":"168","author":"Tastemel","year":"2015","journal-title":"J. Lumin."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.jphotochem.2014.12.005","article-title":"Novel phthalocyanines bearing 7-oxy-3-(3,5-difluorophenyl)coumarin moieties: Synthesis, characterization, photophysical and photochemical properties","volume":"300","author":"Erdogan","year":"2015","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"311","DOI":"10.1016\/j.dyepig.2016.06.002","article-title":"Synthesis, characterization and electrochemical properties of tetra 7-oxy-3-biphenylcoumarin substituted metal-free, zinc(II), cobalt(II) and indium(III) phthalocyanines","volume":"133","author":"Gok","year":"2016","journal-title":"Dyes Pigment."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1016\/j.poly.2012.03.009","article-title":"Synthesis and characterization of metallo phthalocyanines bearing 7-oxy-3-(4-pyridyl)coumarin substituents and their supramolecular structures with vanadyl bis(acetylacetonate)","volume":"38","author":"Esenpinar","year":"2012","journal-title":"Polyhedron"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"1868","DOI":"10.1016\/j.jorganchem.2011.02.029","article-title":"Synthesis, characterization, spectroscopic and electrochemical properties of phthalocyanines substituted with four 3-ferrocenyl-7-oxycoumarin moieties","volume":"696","author":"Esenpinar","year":"2011","journal-title":"J. Organomet. Chem."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/j.ica.2011.03.066","article-title":"Synthesis, characterization, photophysical and photochemical properties of 7-oxy-3-methyl-4-phenylcoumarin-substituted indium phthalocyanines","volume":"373","author":"Piskin","year":"2011","journal-title":"Inorg. Chim. Acta"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"502","DOI":"10.1016\/j.saa.2012.06.029","article-title":"Synthesis and investigation on photophysical and photochemical properties of 7-oxy-3-methyl-4-phenylcoumarin bearing zinc phthalocyanines","volume":"97","author":"Piskin","year":"2012","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"2689","DOI":"10.1016\/j.poly.2010.06.016","article-title":"Derivatizable novel \u03b2-tetra 7-oxycoumarin-3-carboxylate substituted metallophthalocyanines: Synthesis and characterization","volume":"29","author":"Dur","year":"2010","journal-title":"Polyhedron"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"379","DOI":"10.1080\/10610278.2010.521829","article-title":"Synthesis, characterisation and electrochemistry of derivatisable novel \u03b1-tetra 7-oxycoumarin-3-carboxylate-substituted metallophthalocyanines","volume":"23","author":"Dur","year":"2011","journal-title":"Supramol. Chem."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"3625","DOI":"10.1016\/j.poly.2008.09.016","article-title":"Synthesis and characterization of novel phthalocyanines bearing quaternizable coumarin","volume":"27","author":"Cakici","year":"2008","journal-title":"Polyhedron"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"171","DOI":"10.1016\/j.jphotochem.2010.05.021","article-title":"Tetra-3-[(2-diethylamino)ethyl]-7-oxo-4-methylcoumarin- substituted zinc phthalocyanines: Synthesis, characterization and aggregation effects on photophysical\/photochemical properties","volume":"213","author":"Durmus","year":"2010","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"608","DOI":"10.1016\/j.saa.2011.03.043","article-title":"Photophysical, photochemical and BSA binding\/BQ quenching properties of quaternizable coumarin containing water soluble zinc phthalocyanine complexes","volume":"79","author":"Esenpinar","year":"2011","journal-title":"Spectrochim. Acta A Mol. Biomol. Spectrosc."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"1102","DOI":"10.3906\/kim-1405-84","article-title":"Synthesis, characterization, and photophysical and photochemical properties of 3-(4-phenyloxy)coumarin containing metallo- and metal-free phthalocyanines","volume":"38","author":"Kartaloglu","year":"2014","journal-title":"Turk. J. Chem."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"624","DOI":"10.1080\/10610270802613596","article-title":"Effects of coumarin substituents on the photophysical properties of newly synthesized phthalocyanine derivatives","volume":"21","author":"Bulut","year":"2009","journal-title":"Supramol. Chem."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1016\/j.dyepig.2007.04.008","article-title":"The synthesis and characterization of novel soluble phthalocyanines substituted with 7-octyloxy-3-(4-oxyphenyl)coumarin moieties","volume":"77","author":"Bulut","year":"2008","journal-title":"Dyes Pigment."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"233","DOI":"10.1016\/j.poly.2008.10.066","article-title":"Synthesis, characterization and fluorescence behavior of new fluorescent probe phthalocyanines bearing coumarin substituents","volume":"28","author":"Camur","year":"2009","journal-title":"Polyhedron"},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"3129","DOI":"10.1016\/j.poly.2009.06.080","article-title":"Synthesis and characterization of novel \u03b1- or \u03b2-tetra[6,7-dihexyloxy-3-(4-oxyphenyl)coumarin]-substituted metal-free and metallo phthalocyanines","volume":"28","author":"Esenpinar","year":"2009","journal-title":"Polyhedron"},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"691","DOI":"10.1142\/S1088424609000905","article-title":"Synthesis, characterization and spectroscopic properties of new fluorescent 7,8-dihexyloxy-3-(4-oxyphenyl)coumarin substituted phthalocyanines","volume":"13","author":"Bulut","year":"2009","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"92","DOI":"10.1016\/j.poly.2012.04.034","article-title":"Highly singlet oxygen generative water-soluble coumarin substituted zinc(II) phthalocyanine photosensitizers for photodynamic therapy","volume":"41","author":"Durmus","year":"2012","journal-title":"Polyhedron"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"2067","DOI":"10.1016\/j.poly.2011.05.023","article-title":"Synthesis and properties of crown ether functionalized coumarin substituted zinc phthalocyanine","volume":"30","author":"Esenpinar","year":"2011","journal-title":"Polyhedron"},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"3873","DOI":"10.1016\/j.jorganchem.2011.08.045","article-title":"Synthesis and electrochemical properties of crown ether functionalized coumarin substituted cobalt and copper phthalocyanines","volume":"696","author":"Esenpinar","year":"2011","journal-title":"J. Organomet. Chem."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"287","DOI":"10.1016\/j.ica.2011.11.014","article-title":"Synthesis, photophysical, photochemical and electrochemical properties of crown ether bearing coumarin substituted phthalocyanines","volume":"383","author":"Camur","year":"2012","journal-title":"Inorg. Chim. Acta"},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"266","DOI":"10.1016\/j.jphotochem.2011.06.007","article-title":"Coumarino-12-crown-4 bearing phthalocyanine photosensitizers for singlet oxygen production","volume":"222","author":"Durmus","year":"2011","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1016\/j.jorganchem.2016.08.009","article-title":"Preparation, characterization and photophysicochemical properties of novel tetra 7-(diethyl 2-methylmalonatoxy)-3-(p-oxyphenyl)coumarin-substituted zinc(II) and indium(III)chloride phthalocyanines","volume":"822","author":"Koksoy","year":"2016","journal-title":"J. Organomet. Chem."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.jphotochem.2015.10.026","article-title":"High photosensitized singlet oxygen generating zinc(II) and indium(III) acetate phthalocyanines containing 6,8-di-tert-butyl-3-(p-oxyphenyl)coumarin groups","volume":"317","author":"Can","year":"2016","journal-title":"J. Photochem. Photobiol. A"},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"304","DOI":"10.1002\/cmdc.201402401","article-title":"Synthesis and in vitro anticancer activity of zinc(II) phthalocyanines conjugated with coumarin derivatives for dual photodynamic and chemotherapy","volume":"10","author":"Zhou","year":"2015","journal-title":"Chem. Med. Chem."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/j.poly.2012.09.055","article-title":"Synthesis, characterization and dielectric properties of novel axial coumarin-substituted titanium(IV) phthalocyanines","volume":"49","author":"Altun","year":"2013","journal-title":"Polyhedron"},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"3192","DOI":"10.1021\/acs.chemrev.6b00476","article-title":"Strategies for corrole functionalization","volume":"117","author":"Barata","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"130","DOI":"10.1002\/asia.200900345","article-title":"Trans-A2B-corroles bearing a coumarin moiety\u2014From synthesis to photophysics","volume":"5","author":"Tasior","year":"2010","journal-title":"Chem. Asian J."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"799","DOI":"10.1021\/op034083q","article-title":"A scalable synthesis of meso-substituted dipyrromethanes","volume":"7","author":"Laha","year":"2003","journal-title":"Org. Process Res. Dev."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"1360","DOI":"10.1142\/S1088424606000739","article-title":"Meso-substituted corroles bearing peripheral donor sites","volume":"10","author":"Gryko","year":"2006","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"7323","DOI":"10.1021\/jo000882k","article-title":"Rational syntheses of porphyrins bearing up to four different meso substituents","volume":"65","author":"Rao","year":"2000","journal-title":"J. Org. Chem."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"3707","DOI":"10.1021\/jo060007k","article-title":"Efficient synthesis of meso-substituted corroles in a H2O\u2013MeOH mixture","volume":"71","author":"Koszarna","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"1011","DOI":"10.1142\/S1088424611003926","article-title":"Corroles bearing diverse coumarin units\u2014Synthesis and optical properties","volume":"15","author":"Tasior","year":"2011","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"7411","DOI":"10.1039\/C4CP05648E","article-title":"New meso-substituted corroles possessing pentafluorophenyl groups\u2014Synthesis and spectroscopic characterization","volume":"17","author":"Bursa","year":"2015","journal-title":"Phys. Chem. Chem. Phys."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"13811","DOI":"10.1039\/c2jm31281f","article-title":"Corroles as anion chemosensors: Exploiting their fluorescence behaviour from solution to solid-supported devices","volume":"22","author":"Santos","year":"2012","journal-title":"J. Mater. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/6\/994\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T18:39:13Z","timestamp":1760207953000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/22\/6\/994"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2017,6,15]]},"references-count":115,"journal-issue":{"issue":"6","published-online":{"date-parts":[[2017,6]]}},"alternative-id":["molecules22060994"],"URL":"https:\/\/doi.org\/10.3390\/molecules22060994","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2017,6,15]]}}}