{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2025,12,3]],"date-time":"2025-12-03T20:38:22Z","timestamp":1764794302437,"version":"build-2065373602"},"reference-count":77,"publisher":"MDPI AG","issue":"19","license":[{"start":{"date-parts":[[2022,9,25]],"date-time":"2022-09-25T00:00:00Z","timestamp":1664064000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Azaheterocycles rings with five and six members are important tools for the obtaining of fluorescent materials and fluorescent sensors. The relevant advances in the synthesis of azaheterocyclic derivatives and their optical properties investigation, particularly in the last ten years, was our main objective on this review. The review is organized according to the size of the azaheterocycle ring, 5-, 6-membered and fused ring azaheterocycles, as well as our recent contribution on this research field. In each case, the reaction pathways with reaction condition and obtained yield, and evaluation of the optical properties of the obtained products were briefly presented.<\/jats:p>","DOI":"10.3390\/molecules27196321","type":"journal-article","created":{"date-parts":[[2022,9,26]],"date-time":"2022-09-26T01:41:58Z","timestamp":1664156518000},"page":"6321","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":15,"title":["A Review on the Synthesis of Fluorescent Five- and Six-Membered Ring Azaheterocycles"],"prefix":"10.3390","volume":"27","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-9871-4156","authenticated-orcid":false,"given":"Gheorghita","family":"Zbancioc","sequence":"first","affiliation":[{"name":"Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd., 700506 Iasi, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4632-5076","authenticated-orcid":false,"given":"Ionel I.","family":"Mangalagiu","sequence":"additional","affiliation":[{"name":"Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd., 700506 Iasi, Romania"},{"name":"Institute of Interdisciplinary Research-CERNESIM Centre, Alexandru Ioan Cuza University of Iasi, 11 Carol I, 700506 Iasi, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9972-5372","authenticated-orcid":false,"given":"Costel","family":"Moldoveanu","sequence":"additional","affiliation":[{"name":"Chemistry Department, Alexandru Ioan Cuza University of Iasi, 11 Carol 1st Bvd., 700506 Iasi, Romania"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2022,9,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"231","DOI":"10.1021\/acs.chemrev.8b00226","article-title":"The Optoelectronic Nose: Colorimetric and Fluorometric Sensor Arrays","volume":"119","author":"Li","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"2963","DOI":"10.1039\/C4CS00370E","article-title":"Cancer Biomarker Detection: Recent Achievements and Challenges","volume":"44","author":"Wu","year":"2015","journal-title":"Chem. Soc. Rev."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"027112","DOI":"10.1088\/1752-7155\/8\/2\/027112","article-title":"Detecting Cancer by Breath Volatile Organic Compound Analysis: A Review of Array-Based Sensors","volume":"8","author":"Queralto","year":"2014","journal-title":"J. Breath Res."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1016\/j.dyepig.2018.01.002","article-title":"Efficient green electroluminescence from 1,3-diphenyl-1H-pyrazolo[3,4-b]quinoxaline dyes in dye-doped polymer based electroluminescent devices","volume":"151","author":"Matusiewicz","year":"2018","journal-title":"Dyes Pigments"},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"891","DOI":"10.1016\/j.ejmech.2006.01.018","article-title":"Synthesis and in vitro antibacterial activity of novel heterocyclic derivatives of 18-nor-equilenin","volume":"41","author":"Karnik","year":"2006","journal-title":"Eur. J. Med. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"587","DOI":"10.1016\/S0039-128X(03)00080-1","article-title":"Azasteroids as antifungals","volume":"68","author":"Burbiel","year":"2003","journal-title":"Steroids"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"1043","DOI":"10.14233\/ajchem.2016.19582","article-title":"Efficient synthesis and characterization of ethyl 7-acetyl-2-substituted 3-(substitutedbenzoyl) indolizine-1-carboxylates for in vitro anticancer activity","volume":"28","author":"Sandeep","year":"2016","journal-title":"Asian J. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"2404","DOI":"10.1021\/acs.jmedchem.8b01689","article-title":"Design and Synthesis of 1,2-Bis(hydroxymethyl)pyrrolo[2,1-a]phthalazine Hybrids as Potent Anticancer Agents that Inhibit Angiogenesis and Induce DNA Interstrand Cross-links","volume":"62","author":"Chang","year":"2019","journal-title":"J. Med. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"26","DOI":"10.1016\/j.ejps.2006.09.006","article-title":"Synthesis of indolizine derivatives with selective antibacterial activity against Mycobacterium tuberculosis","volume":"30","author":"Gundersen","year":"2007","journal-title":"Eur. J. Pharm. Sci."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"2214","DOI":"10.1016\/j.bmc.2012.02.025","article-title":"Generation and exploration of new classes of antitubercular agents: The optimization of oxazolines, oxazoles, thiazolines, thiazoles to imidazo[1,2-a]pyridines and isomeric 5,6-fused scaffolds","volume":"20","author":"Moraski","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref_11","first-page":"53","article-title":"Synthesis and antioxidant activity of 3,3\u2032-diselanediylbis (N,N-disubstituted indolizine-1-carboxamide) and derivatives","volume":"61","author":"Narajji","year":"2008","journal-title":"S. Afr. J. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"730","DOI":"10.1111\/cbdd.12119","article-title":"Indolizine derivatives as HIV\u20131 VIF\u2013ElonginC interaction inhibitors","volume":"81","author":"Huang","year":"2013","journal-title":"Chem. Biol. Drug. Des."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"29051","DOI":"10.1039\/C8RA02297F","article-title":"Small-molecule fluorescent probes and their design","volume":"8","author":"Fu","year":"2018","journal-title":"RSC Adv."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"277","DOI":"10.1007\/s10895-007-0267-0","article-title":"Spectral-Luminescent Properties of 12-Oximino Derivatives of 8-AZA-D-Homogona-12,17a-Diones and their Concentration Dependence","volume":"18","author":"Bagnich","year":"2008","journal-title":"J. Fluoresc."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1007\/s10895-006-0097-5","article-title":"Delayed Fluorescence and Phosphorescence of 8-Aza-d-Homogonane in the Gas and Condensed Phases","volume":"16","author":"Borisevich","year":"2006","journal-title":"J. Fluoresc."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"357","DOI":"10.1023\/A:1020596210145","article-title":"Specific fluorescence properties and picosecond transient absorption of 8-azasteroids","volume":"9","author":"Akhrem","year":"1999","journal-title":"J. Fluoresc."},{"key":"ref_17","first-page":"470","article-title":"Synthesis, structure, antimycobacterial and anticancer evaluation of new pyrrolo-(phenanthroline) derivatives","volume":"31","author":"Shova","year":"2016","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"562","DOI":"10.1016\/j.ejmech.2019.07.019","article-title":"An insight into the medicinal perspective of synthetic analogs of indole: A review","volume":"180","author":"Thanikachalam","year":"2019","journal-title":"Eur. J. Med. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"2318","DOI":"10.1016\/j.bmc.2015.03.077","article-title":"New indolizines with phenanthroline skeleton: Synthesis, structure, antimycobacterial and anticancer evaluation","volume":"23","author":"Danac","year":"2015","journal-title":"Bioorg. Med. Chem."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2","DOI":"10.4103\/0975-7406.171694","article-title":"Current status of pyrazole and its biological activities","volume":"8","author":"Naim","year":"2016","journal-title":"J. Pharm. Bioallied Sci."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1742","DOI":"10.1039\/C7MD00067G","article-title":"Imidazoles as potential anticancer agents","volume":"8","author":"Ali","year":"2017","journal-title":"MedChemComm"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1080\/14756366.2016.1190711","article-title":"Hybrid imidazole (benzimidazole)\/pyridine (quinoline) derivatives and evaluation of theiranticancer and antimycobacterialactivity","volume":"31","author":"Mantu","year":"2016","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"6208","DOI":"10.1016\/j.bmc.2012.09.013","article-title":"The therapeutic journey of benzimidazoles: A review","volume":"20","author":"Bansal","year":"2012","journal-title":"Bioorg. Med. Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"3511","DOI":"10.1016\/j.bmc.2019.07.005","article-title":"1,2,3-Triazole-containing hybrids as leads in medicinal chemistry: A recent overview","volume":"27","author":"Bozorov","year":"2019","journal-title":"Bioorg. Med. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"3","DOI":"10.2174\/1871522218666180525100850","article-title":"Tetrazoles: Synthesis and biological activity","volume":"18","author":"Kaushik","year":"2018","journal-title":"Immunol. Endocr. Metab. Agents Med. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"1869","DOI":"10.1039\/D0QO00405G","article-title":"Straight access to highly fluorescent angular indolocarbazoles via merging Au- and Mo-catalysis","volume":"7","author":"Tapia","year":"2020","journal-title":"Org. Chem. Front. J."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"11124","DOI":"10.1021\/acs.joc.0c01042","article-title":"Transition-Metal-Free C\u2013H\/C\u2013Li Coupling of Nonaromatic 2H-Imidazole 1-Oxides with Pentafluorophenyl Lithium in the Design of Novel Fluorophores with Intramolecular Charge Transfer Effect","volume":"85","author":"Moseev","year":"2020","journal-title":"J. Org. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.dyepig.2016.02.001","article-title":"Multi-controllable properties of an antipyrine-based diarylethene and its high selectivity for recognition of Al3+","volume":"129","author":"Pu","year":"2016","journal-title":"Dyes Pigments"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"190","DOI":"10.1021\/cr0783840","article-title":"Fluorescent labeling of biomolecules with organic probes","volume":"109","author":"Sameiro","year":"2009","journal-title":"Chem. Rev."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"475","DOI":"10.1038\/nchembio.1296","article-title":"Chemical reporters for biological discovery","volume":"9","author":"Grammel","year":"2013","journal-title":"Nat. Chem. Biol."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"4764","DOI":"10.1021\/cr400355w","article-title":"Cellular incorporation of unnatural amino acids and bioorthogonal labeling of proteins","volume":"114","author":"Lang","year":"2014","journal-title":"Chem. Rev."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"4","DOI":"10.1021\/acs.bioconjchem.0c00606","article-title":"Design and application of receptor-targeted fluorescent probes based on small molecular fluorescent Dyes","volume":"32","author":"Zhang","year":"2021","journal-title":"Bioconj. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"9243","DOI":"10.1021\/acs.chemrev.0c01176","article-title":"Photoluminescent nanoparticles for chemical and biological analysis and imaging","volume":"121","author":"Algar","year":"2021","journal-title":"Chem. Rev."},{"key":"ref_34","doi-asserted-by":"crossref","unstructured":"Li, Z., Li, Y., Chang, W., Pang, S., Li, X., Duan, L., and Zhang, Z. (2022). Synthesis and Fluorescent Properties of Aminopyridines and the Application in \u201cClick and Probing\u201d. Molecules, 27.","DOI":"10.3390\/molecules27051596"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1039\/c2pp25261a","article-title":"Acridinyl methyl esters as photoactive precursors in the release of neurotransmitteramino acids","volume":"12","author":"Piloto","year":"2013","journal-title":"Photochem. Photobiol. Sci."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"7640","DOI":"10.1039\/C6TC02591A","article-title":"Aromatic azaheterocycle-cored luminogens with tunable physical properties via nitrogen atoms for sensing strong acids","volume":"4","author":"Tang","year":"2016","journal-title":"J. Mater. Chem. C"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"5231","DOI":"10.1002\/ejoc.201200688","article-title":"Arylamine-Modified Thiazoles as Donor\u2013Acceptor Dyes: Quantum Chemical Evaluation of the Charge-Transfer Process and Testing as Ligands in Ruthenium(II) Complexes","volume":"27","author":"Menzel","year":"2012","journal-title":"Eur. J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1710","DOI":"10.1080\/10406638.2020.1804411","article-title":"Ultra-High Stokes Shift in Polycyclic Chromeno[2,3-b]Indoles","volume":"42","author":"Rajbongshi","year":"2022","journal-title":"Polycycl. Aromat. Compd."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"709","DOI":"10.1039\/D0SC04725B","article-title":"Unusual light-driven amplification through unexpected regioselective photogeneration of five-membered azaheterocyclic AIEgen","volume":"12","author":"Li","year":"2021","journal-title":"Chem. Sci."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"476","DOI":"10.2174\/15734064113096660070","article-title":"Synthesis and in vitro analysis of novel dihydroxyacetophenone derivatives with antimicrobial and antitumor activities","volume":"10","author":"Zbancioc","year":"2014","journal-title":"Med. Chem."},{"key":"ref_41","doi-asserted-by":"crossref","unstructured":"Antoci, V., Oniciuc, L., Amariucai-Mantu, D., Moldoveanu, C., Mangalagiu, V., Amarandei, A.M., Lungu, C.N., Dunca, S., Mangalagiu, I.I., and Zbancioc, G. (2021). Benzoquinoline Derivatives: A Straightforward and Efficient Route to Antibacterial and Antifungal Agents. Pharmaceuticals, 14.","DOI":"10.3390\/ph14040335"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"230","DOI":"10.1080\/14756366.2018.1550085","article-title":"Synthesis, molecular modelling and anticancer evaluation of new pyrrolo[1,2-b]pyridazine and pyrrolo[2,1-a]phthalazinederivatives","volume":"34","author":"Popovici","year":"2019","journal-title":"J. Enzym. Inhib. Med. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"9470","DOI":"10.1002\/anie.201909706","article-title":"Time-Dependent Photodynamic Therapy for Multiple Targets: A Highly Efficient AIE-Active Photosensitizer for Selective Bacterial Elimination and Cancer Cell Ablation","volume":"59","author":"Li","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2941","DOI":"10.1021\/acs.orglett.7b01175","article-title":"Synthesis of Benzoquinolizinium Salts by Rh(III)-Catalyzed Cascade Double N-Annulation Reactions of Allylamines, Diarylacetylenes, and HBF4","volume":"19","author":"Han","year":"2017","journal-title":"Org. Lett."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"4330","DOI":"10.1002\/slct.202100804","article-title":"Synthesis of 1H-Pyrazolo[3,4-b]quinoxaline Derivatives by Modification of the Regiospecific Reaction\u2013the Influence of the Microwave Field","volume":"6","author":"Wojtasik","year":"2021","journal-title":"ChemistrySelect"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"e202100780","DOI":"10.1002\/ajoc.202100780","article-title":"A New Entry to Purely Organic Thermally Activated Delayed Fluorescence Emitters Based on Pyrido[2,3-b]pyrazine-Dihydrophenazasilines Donor-Acceptor Dyad","volume":"11","author":"Goya","year":"2022","journal-title":"Asian J. Org. Chem."},{"key":"ref_47","first-page":"1345","article-title":"Palladium-Catalyzed Cross-Coupling Reactions of 7-Bromo-2,3-diphenylpyrido[2,3-b]pyrazine","volume":"8","author":"Yin","year":"2005","journal-title":"Synthesis"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"1121","DOI":"10.1080\/00397911.2021.1873383","article-title":"A general method for the synthesis of structurally diverse quinoxalines and pyrido-pyrazine derivatives using camphor sulfonic acid as an efficient organo-catalyst at room temperature","volume":"51","author":"Kaur","year":"2021","journal-title":"Synth. Commun."},{"key":"ref_49","first-page":"49","article-title":"Synthesis and fluorescence of 1-[7-(4-nitrobenzoyl)-3-(biphenyl-4-yl)pyrrolo[1,2-c]pyrimidin-5-yl]ethanone","volume":"77","author":"Tatu","year":"2015","journal-title":"UPB Bull. Sci."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"643","DOI":"10.1016\/j.arabjc.2016.09.013","article-title":"Ungureanu, E.M. Synthesis and fluorescence of new 3-biphenylpyrrolo[1,2-c]pyrimidines","volume":"10","author":"Tatu","year":"2017","journal-title":"Arab. J. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"108023","DOI":"10.1016\/j.dyepig.2019.108023","article-title":"Influence of the chemical structure and solvent polarity on the fluorescence of 3-aryl-7-benzoyl-pyrrolo [1,2-c]pyrimidines","volume":"174","author":"Ungureanu","year":"2020","journal-title":"Dyes Pigments"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"94551","DOI":"10.1039\/C5RA17755C","article-title":"A new heterocyclic skeleton with highly tunable absorption\/emission wavelength via H-bonding","volume":"5","author":"Tomashenko","year":"2015","journal-title":"RSC Adv."},{"key":"ref_53","unstructured":"Zugravescu, I., and Petrovanu, M. (1977). N-Ylid Chemistry, McGraw Hill Higher Education. ISBN-13: 9780070730809."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"644","DOI":"10.2174\/157018010792929504","article-title":"Design, synthesis and in vitro anticancer activity of a new class of dual DNA intercalators","volume":"7","author":"Zbancioc","year":"2010","journal-title":"Lett. Drug Des. Discov."},{"key":"ref_55","doi-asserted-by":"crossref","unstructured":"Al Matarneh, C.M., Amarandi, R.M., Craciun, A.M., Mangalagiu, I.I., Zbancioc, G., and Danac, R. (2020). Design, Synthesis, Molecular Modelling and Anticancer Activities of New Fused Phenanthrolines. Molecules, 25.","DOI":"10.3390\/molecules25030527"},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.mehy.2013.10.024","article-title":"Hybrid anticancer 1,2-diazine derivatives with multiple mechanism of action. Part 3","volume":"82","author":"Antoci","year":"2014","journal-title":"Med. Hypotheses"},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"154","DOI":"10.2174\/0929867326666181220094229","article-title":"Hybrid Imidazole-Pyridine Derivatives: An Approach to Novel Anticancer DNA Intercalators","volume":"27","author":"Lungu","year":"2020","journal-title":"Curr. Med. Chem."},{"key":"ref_58","first-page":"287","article-title":"Microwave assisted synthesis of six member ring azaheterocycles and their antimycobacterial and anticancer evaluation","volume":"71","author":"Ciobanu","year":"2020","journal-title":"Rev. Chim."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"344","DOI":"10.2174\/1871526514666140217144707","article-title":"Design, synthesis and antituberculosis activity of some new pyridazine derivatives: Bis-pyridazine. Part IV","volume":"13","author":"Mantu","year":"2013","journal-title":"Infect. Disord.-Drug Targets"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"207","DOI":"10.4155\/fmc-2019-0063","article-title":"Bis-(imidazole\/benzimidazole)-pyridine derivatives: Synthesis, structure and antimycobacterial activity. Part XII","volume":"12","author":"Antoci","year":"2020","journal-title":"Future Med. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"5164","DOI":"10.1016\/j.ejmech.2010.08.029","article-title":"Synthesis and antituberculosis activity of some new pyridazine derivatives. Part II","volume":"45","author":"Mantu","year":"2010","journal-title":"Eur. J. Med. Chem."},{"key":"ref_62","first-page":"114","article-title":"Azine, New Molecules with Azaheterocycles Skeleton of Potential Interest in Leishmaniasis","volume":"7","author":"Mangalagiu","year":"2018","journal-title":"Org. Chem. Curr. Res."},{"key":"ref_63","first-page":"0804","article-title":"Microwave-Assisted Synthesis of Highly Fluorescent Pyrrolopyridazine Derivatives","volume":"5","author":"Zbancioc","year":"2006","journal-title":"Synlett"},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"4298","DOI":"10.1016\/j.tet.2010.04.050","article-title":"Pyrrolodiazine derivatives as blue organic luminophores: Synthesis and properties. Part 3","volume":"66","author":"Zbancioc","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"3165","DOI":"10.1021\/jp311396m","article-title":"Conformational effects on the lowest excited states of benzoyl-pyrrolopyridazine: Insights from PCM time-dependent DFT","volume":"117","author":"Maftei","year":"2013","journal-title":"J. Phys. Chem. A"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"278","DOI":"10.1016\/j.tet.2009.10.110","article-title":"Pyrrolopyridazine derivatives as blue organic luminophores: Synthesis and properties. Part 2","volume":"66","author":"Zbancioc","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_67","doi-asserted-by":"crossref","unstructured":"Moldoveanu, C., Amariucai-Mantu, D., Mangalagiu, V., Antoci, V., Maftei, D., Mangalagiu, I.I., and Zbancioc, G. (2019). Microwave Assisted Reactions of Fluorescent Pyrrolodiazine Building Blocks. Molecules, 24.","DOI":"10.3390\/molecules24203760"},{"key":"ref_68","doi-asserted-by":"crossref","unstructured":"Moldoveanu, C., Mangalagiu, I., and Zbancioc, G. (2021). Fluorescent Azasteroids through Ultrasound Assisted Cycloaddition Reactions. Molecules, 26.","DOI":"10.3390\/molecules26165098"},{"key":"ref_69","doi-asserted-by":"crossref","unstructured":"Zbancioc, G., Ciobanu, C.-I., Mangalagiu, I.I., and Moldoveanu, C. (2022). Ultrasound-Assisted Synthesis of Fluorescent Azatetracyclic Derivatives: An Energy-Efficient Approach. Molecules, 27.","DOI":"10.3390\/molecules27103180"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"113196","DOI":"10.1016\/j.molliq.2020.113196","article-title":"Synthesis and photophysical insights of new fused N-heterocyclic derivatives with isoquinoline skeleton","volume":"310","author":"Gherasim","year":"2020","journal-title":"J. Mol. Liq."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"6","DOI":"10.1016\/j.jlumin.2018.03.005","article-title":"Steady state and time resolved fluorescence studies of new indolizine with phenanthroline skeleton derivatives","volume":"199","author":"Airinei","year":"2018","journal-title":"J. Lumin."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"901","DOI":"10.2298\/JSC200819057A","article-title":"Synthesis and properties of new fused pyrrolo-1,10-phenanthroline type derivatives","volume":"86","author":"Rosca","year":"2021","journal-title":"J. Serb. Chem. Soc."},{"key":"ref_73","doi-asserted-by":"crossref","unstructured":"Doroftei, C., Carlescu, A., Leontie, L., Danac, R., and Al-Matarneh, C.M. (2022). Structural, Electrical and Optical Properties of Pyrrolo[1,2-i][1,7] Phenanthroline-Based Organic Semiconductors. Materials, 15.","DOI":"10.3390\/ma15051684"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"8215","DOI":"10.1016\/j.tet.2016.10.052","article-title":"Pyridyl-indolizine derivatives as DNA binders and pH-sensitive fluorescent dyes","volume":"72","author":"Marangoci","year":"2016","journal-title":"Tetrahedron"},{"key":"ref_75","first-page":"903","article-title":"Fluorescent Conjugates: pH Stability, Dye-DNA Interaction and Biological Activity","volume":"61","author":"Gradinaru","year":"2010","journal-title":"Rev. Chim."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"968","DOI":"10.1039\/C7PY01668A","article-title":"Novel cyclodextrin-based pH-sensitive supramolecular host\u2013guest assembly for staining acidic cellular organelles","volume":"9","author":"Pricope","year":"2018","journal-title":"Polym. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","unstructured":"Sardaru, M.-C., Carp, O., Ursu, E.-L., Craciun, A.-M., Cojocaru, C., Silion, M., Kovalska, V., Mangalagiu, I., Danac, R., and Rotaru, A. (2020). Cyclodextrin Encapsulated pH Sensitive Dyes as Fluorescent Cellular Probes: Self-Aggregation and In Vitro Assessments. Molecules, 25.","DOI":"10.3390\/molecules25194397"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/19\/6321\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T00:39:21Z","timestamp":1760143161000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/19\/6321"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,9,25]]},"references-count":77,"journal-issue":{"issue":"19","published-online":{"date-parts":[[2022,10]]}},"alternative-id":["molecules27196321"],"URL":"https:\/\/doi.org\/10.3390\/molecules27196321","relation":{},"ISSN":["1420-3049"],"issn-type":[{"type":"electronic","value":"1420-3049"}],"subject":[],"published":{"date-parts":[[2022,9,25]]}}}