{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,21]],"date-time":"2026-09-21T01:39:37Z","timestamp":1789954777661,"version":"4.0.1"},"reference-count":89,"publisher":"MDPI AG","issue":"8","license":[{"start":{"date-parts":[[2014,7,25]],"date-time":"2014-07-25T00:00:00Z","timestamp":1406246400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/3.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Materials"],"abstract":"<jats:p>Three asymmetric amino-substituted perylene bisimide dyes with different  n-alkyl chain lengths (n = 6, 12, or 18), 1-(N,N-dialkylamino)perylene bisimides (1a\u20131c), were synthesized under mild condition in high yields and were characterized by 1H NMR, 13C NMR (nuclear magnetic resonance), HRMS (High Resolution Mass Spectrometer), UV-Vis and fluorescence spectra, as well as cyclic voltammetry (CV). These molecules show intense green color in both solution and solid state and are highly soluble in dichloromethane and even in nonpolar solvents, such as hexane. The shapes of the absorption spectra of 1a\u20131c in solid state and in solution were found to be virtually the same, indicating that the long alkyl chains could efficiently prevent aggregation. They exhibit a unique charge transfer emission in the near-infrared region, of which the peak wavelengths show strong solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show larger dipole moment changes than that of 1-aminoperylene bisimide (2). Furthermore, all of the compounds exhibit two quasi-reversible one-electron oxidations and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory (DFT) calculations performed on these dyes are reported in order to rationalize their molecular structures and electronic properties.<\/jats:p>","DOI":"10.3390\/ma7085488","type":"journal-article","created":{"date-parts":[[2014,7,25]],"date-time":"2014-07-25T10:54:02Z","timestamp":1406285642000},"page":"5488-5506","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":29,"title":["Green Perylene Bisimide Dyes: Synthesis, Photophysical and Electrochemical Properties"],"prefix":"10.3390","volume":"7","author":[{"given":"Che-Wei","family":"Chang","sequence":"first","affiliation":[{"name":"Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Hsing-Yang","family":"Tsai","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-2193-688X","authenticated-orcid":false,"given":"Kew-Yu","family":"Chen","sequence":"additional","affiliation":[{"name":"Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2014,7,25]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"6363","DOI":"10.1002\/anie.200461324","article-title":"High-mobility air-stable n-type semiconductors with processing versatility: Dicyanoperylene-3,4:9,10-bis(dicarboximides)","volume":"43","author":"Jones","year":"2004","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_2","first-page":"1","article-title":"High-mobility ambipolar transistors and high-gain inverters from a donor-acceptor copolymer semiconductor","volume":"21","author":"Kim","year":"2009","journal-title":"Adv. Mater."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"5109","DOI":"10.1039\/c1cc10321k","article-title":"Naphthalene and perylene diimides for organic transistors","volume":"47","author":"Stolte","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"7811","DOI":"10.1039\/c1jm11091h","article-title":"Air stable electron-transporting and ambipolar bay substituted perylene bisimides","volume":"21","author":"Reghu","year":"2011","journal-title":"J. Mater. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1296","DOI":"10.1021\/cr0501543","article-title":"Electron and ambipolar transport in organic field-effect transistors","volume":"107","author":"Zaumseil","year":"2007","journal-title":"Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"3366","DOI":"10.1021\/cm047851g","article-title":"Organic thin film transistors based on cyclohexyl-substituted organic semiconductors","volume":"17","author":"Locklin","year":"2005","journal-title":"Chem. Mater."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"329","DOI":"10.1016\/j.dyepig.2013.05.011","article-title":"Synthesis and characterization of new electron acceptor perylene diimide molecules for photovoltaic applications","volume":"99","author":"Kozma","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"96","DOI":"10.1039\/B512373A","article-title":"Poly(2,7-carbazole) and perylene tetracarboxydiimide: A promising donor\/acceptor pair for polymer solar cells","volume":"16","author":"Li","year":"2006","journal-title":"J. Mater. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"182","DOI":"10.1016\/j.dyepig.2011.03.022","article-title":"Effect of side chain substituents on the electron injection abilities of unsymmetrical perylene diimide dyes","volume":"91","author":"Zafer","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"386","DOI":"10.1021\/ja2080482","article-title":"Competition between singlet fission and charge separation in solution-processed blend films of 6,13-bis(triisopropylsilylethynyl)-pentacene with sterically-encumbered perylene-3,4:9,10-bis(dicarboximide)s","volume":"134","author":"Ramanan","year":"2012","journal-title":"J. Am. Chem. Soc."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1971","DOI":"10.1021\/ol070556s","article-title":"Electron-donating perylene tetracarboxylic acids for dye-sensitized solar cells","volume":"9","author":"Shibano","year":"2007","journal-title":"Org. Lett."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"160","DOI":"10.1016\/j.dyepig.2013.01.020","article-title":"Perylene diimides based materials for organic solar cells","volume":"98","author":"Kozma","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"2708","DOI":"10.1039\/b004063k","article-title":"Synthesis of novel multi-chromophoric soluble perylene derivatives and their photosensitizing properties with wide spectral response for SnO2 nanoporous electrode","volume":"10","author":"Tian","year":"2000","journal-title":"J. Mater. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"5509","DOI":"10.1039\/C0CC05448H","article-title":"Synthesis of annulated thiophene perylene bisimide analogues: Their applications to bulk heterojunction organic solar cells","volume":"47","author":"Choi","year":"2011","journal-title":"Chem. Commun."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"2386","DOI":"10.1021\/jo2001963","article-title":"Perylene-3,4,9,10-tetracarboxylic acid diimides: Synthesis, physical properties, and use in organic electronics","volume":"76","author":"Huang","year":"2011","journal-title":"J. Org. Chem."},{"key":"ref_16","first-page":"1751","article-title":"Solar cells based on perylene bisimide derivatives","volume":"20","author":"Wang","year":"2008","journal-title":"Prog. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"4226","DOI":"10.1039\/c2cc30948c","article-title":"Phosphorescent perylene imides","volume":"48","author":"Ventura","year":"2012","journal-title":"Chem. Commun."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"169","DOI":"10.1016\/j.dyepig.2006.01.031","article-title":"Properties of novel perylene-3,4:9,10-tetracarboxidiimide-centred dendrimers and their application as emitters in organic electroluminescence devices","volume":"74","author":"Matsui","year":"2007","journal-title":"Dyes Pigm."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"228","DOI":"10.1016\/j.dyepig.2013.04.035","article-title":"Tuning of the color of the emitted light from new polyperyleneimides containing oxadiazole and siloxane moieties","volume":"99","author":"Damaceanu","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"748","DOI":"10.1016\/j.dyepig.2012.11.015","article-title":"New organic-inorganic hybrid materials based on perylene diimide\u2013polyhedral oligomeric silsesquioxane dyes with reduced quenching of the emission in the solid state","volume":"96","author":"Lucenti","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"7658","DOI":"10.1016\/j.polymer.2005.05.117","article-title":"Dendron-functionalized perylene diimides with carrier-transporting ability for red luminescent materials","volume":"46","author":"Pan","year":"2005","journal-title":"Polymer"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"10810","DOI":"10.1021\/ja047176b","article-title":"Ultrafast aggregate-to-aggregate energy transfer within self-assembled light-harvesting columns of zinc phthalocyanine tetrakis(perylenediimide)","volume":"126","author":"Li","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"12268","DOI":"10.1021\/ja0460514","article-title":"Combining light-harvesting and charge separation in a self-assembled artificial photosynthetic system based on perylenediimide chromophores","volume":"126","author":"Rybtchinski","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"6616","DOI":"10.1002\/anie.200802007","article-title":"Toward fluorescent memories with nondestructive readout: Photoswitching of fluorescence by intramolecular electron transfer in a diaryl ethene-perylene bisimide photochromic system","volume":"47","author":"Berberich","year":"2008","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1016\/j.dyepig.2010.03.020","article-title":"A photochromic diarylethene dyad based on perylene diimide","volume":"89","author":"Tan","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"5577","DOI":"10.1021\/ja0398215","article-title":"Making a molecular wire: Charge and spin transport through para-phenylene oligomers","volume":"126","author":"Weiss","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"8952","DOI":"10.1021\/ja902258g","article-title":"Toward an n-type molecular wire: Electron hopping within linearly linked perylenediimide oligomers","volume":"131","author":"Wilson","year":"2009","journal-title":"J. Am. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"34","DOI":"10.1016\/j.dyepig.2011.11.009","article-title":"Facile synthesis and characterization of novel coronene chromophores and their application to LCD color filters","volume":"94","author":"Choi","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"166","DOI":"10.1016\/j.dyepig.2010.06.003","article-title":"The synthesis of thermally-stable red dyes for LCD color filters and analysis of their aggregation and spectral properties","volume":"88","author":"Sakong","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"10871","DOI":"10.1021\/jp2064968","article-title":"Helical assembly induced by hydrogen bonding from chiral carboxylic acids based on perylene bisimides","volume":"115","author":"Lu","year":"2011","journal-title":"J. Phys. Chem. B"},{"key":"ref_31","first-page":"1564","article-title":"Perylene bisimide dyes as versatile building blocks for functional supramolecular architectures","volume":"14","year":"2004","journal-title":"Chem. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1910","DOI":"10.1021\/ar9001735","article-title":"Self-assembly strategies for integrating light harvesting and charge separation in artificial photosynthetic systems","volume":"42","author":"Wasielewski","year":"2009","journal-title":"Acc. Chem. Res."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"502","DOI":"10.1016\/j.dyepig.2013.06.004","article-title":"Interpreting the near-infrared reflectance of a series of perylene pigments","volume":"99","author":"Kaur","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"332","DOI":"10.1016\/j.dyepig.2011.04.015","article-title":"Design and synthesis of novel fluorescence sensing perylene diimides based on photoinduced electron transfer","volume":"91","author":"Georgiev","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1002\/(SICI)1099-0690(200001)2000:2<365::AID-EJOC365>3.0.CO;2-R","article-title":"Novel fluorescent dyes by the extension of the core of perylenetetracarboxylic bisimides","volume":"2","author":"Langhals","year":"2000","journal-title":"Eur. J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"260","DOI":"10.1016\/j.dyepig.2012.04.015","article-title":"The synthesis, morphology and liquid-crystalline property of polysiloxane-modified perylene derivative","volume":"95","author":"Liang","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"106","DOI":"10.1016\/j.dyepig.2010.12.012","article-title":"New imides based on perylene and siloxane derivatives","volume":"90","author":"Cazacu","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"1108","DOI":"10.1016\/j.dyepig.2011.06.011","article-title":"Near-infrared reflective properties of perylene derivatives","volume":"92","author":"Kaur","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"149","DOI":"10.1016\/j.cclet.2011.10.017","article-title":"Synthesis of highly fluorescent and water soluble perylene bisimide","volume":"23","author":"Boobalan","year":"2012","journal-title":"Chin. Chem. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"129","DOI":"10.1016\/j.dyepig.2012.12.008","article-title":"PEGylated nanoparticles of diperylene bisimides with high efficiency of 1O2 generation","volume":"97","author":"Cui","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"450","DOI":"10.1016\/j.dyepig.2013.04.006","article-title":"Facile synthesis and controllable bromination of asymmetrical intermediates of perylene monoanhydride\/monoimide diester","volume":"98","author":"Wang","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"456","DOI":"10.1016\/j.dyepig.2013.05.033","article-title":"Asymmetric perylene bisimide dyes with strong solvatofluorism","volume":"99","author":"Luo","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"244","DOI":"10.1016\/j.dyepig.2012.12.015","article-title":"Construction of well-defined butadiynylene-linked perylene bisimide arrays via cross-coupling","volume":"97","author":"Kang","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"9163","DOI":"10.1021\/ac301830a","article-title":"Efficient fluorescence \u201cturn-on\u201d sensing of dissolved oxygen by electrochemical switching","volume":"84","author":"Shin","year":"2012","journal-title":"Anal. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"7369","DOI":"10.1021\/ac401272a","article-title":"Single-molecule study on polymer diffusion in a melt state: Effect of chain topology","volume":"85","author":"Habuchi","year":"2013","journal-title":"Anal. Chem."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1704","DOI":"10.3390\/ma6051704","article-title":"Fabrication of a poly(3-octylthiophene-2,5-diyl) electrochemiluminescence device assisted by perylene","volume":"6","author":"Daimon","year":"2013","journal-title":"Materials"},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Sharma, G.D., Kurchania, R., Ball, R.J., Roy, M.S., and Mikroyannidis, J.A. (2012). Effect of deoxycholic acid on the performance of liquid electrolyte dye-sensitized solar cells using a perylene monoimide derivative. Int. J. Photoenergy, 2012.","DOI":"10.1155\/2012\/983081"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"327","DOI":"10.3390\/molecules19010327","article-title":"1,6- and 1,7-Regioisomers of asymmetric and symmetric perylene bisimides: Synthesis, characterization and optical properties","volume":"19","author":"Tsai","year":"2014","journal-title":"Molecules"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2747","DOI":"10.1016\/j.jlumin.2012.05.017","article-title":"Spectral characteristics and fluorescence quenching of N,N\u2019-bis(4-pyridyl)-3,4:9,10-perylenebis(dicarboximide) (BPPD)","volume":"132","author":"Alamry","year":"2012","journal-title":"J. Lumin."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"103","DOI":"10.1016\/j.jlumin.2014.01.031","article-title":"Synthesis and optical properties of novel asymmetric perylene bisimides","volume":"149","author":"Tsai","year":"2014","journal-title":"J. Lumin."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1358","DOI":"10.1021\/ac3030009","article-title":"Direct and freely switchable detection of target genes engineered by reduced graphene oxide-poly(m-aminobenzenesulfonic acid) nanocomposite via synchronous pulse electrosynthesis","volume":"85","author":"Yang","year":"2013","journal-title":"Anal. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"2667","DOI":"10.1021\/ac302971x","article-title":"In situ formation of metal coordination polymer: A strategy for fluorescence turn-on assay of acetylcholinesterase activity and inhibitor screening","volume":"85","author":"Liao","year":"2013","journal-title":"Anal. Chem."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"330","DOI":"10.1016\/j.dyepig.2012.01.010","article-title":"Binding interaction between serum albumins and perylene-3,4,9,10-tetracarboxylate\u2014A spectroscopic investigation","volume":"94","author":"Naveenraj","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"4019","DOI":"10.1016\/j.tetlet.2013.05.076","article-title":"A colorimetric and fluorescent sensor based on PBIs for palladium detection","volume":"54","author":"Zhang","year":"2013","journal-title":"Tetrahedron Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"387","DOI":"10.1016\/j.jlumin.2013.10.009","article-title":"Fabrication of luminescent perylene bisimide nanorods","volume":"146","author":"Boobalan","year":"2014","journal-title":"J. Lumin."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"4637","DOI":"10.1021\/ja074675e","article-title":"Organic n-channel transistors based on core-cyanated perylene carboxylic diimide derivatives","volume":"130","author":"Weitz","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"15259","DOI":"10.1021\/ja075242e","article-title":"Tuning orbital energetics in arylene diimide semiconductors. Materials design for ambient stability of n-type charge transport","volume":"129","author":"Jones","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"5959","DOI":"10.1016\/j.tetlet.2010.09.029","article-title":"1,7-Dinitroperylene bisimides: Facile synthesis and characterization as n-type organic semiconductors","volume":"51","author":"Chen","year":"2010","journal-title":"Tetrahedron Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"410","DOI":"10.1016\/j.dyepig.2012.01.024","article-title":"Colorimetric and ratiometric luorescent chemosensor for fluoride ion based on perylene diimide derivatives","volume":"94","author":"Chen","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"450","DOI":"10.1016\/j.dyepig.2012.05.009","article-title":"Facile synthesis and replacement reactions of mono-substituteded perylene bisimide dyes","volume":"95","author":"Kong","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"3007","DOI":"10.1021\/jo100231j","article-title":"Core-perfluoroalkylated perylene diimides and naphthalene diimides: Versatile synthesis, solubility, electrochemistry, and optical properties","volume":"75","author":"Yuan","year":"2010","journal-title":"J. Org. Chem."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"529","DOI":"10.1021\/ol703046w","article-title":"Air-stable n-type semiconductor: Core-perfluoroalkylated perylene bisimides","volume":"10","author":"Li","year":"2008","journal-title":"Org. Lett."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"4323","DOI":"10.1021\/jo050001f","article-title":"Photophysical and electrochemical properties of 1,7-diaryl-substituted perylene diimides","volume":"70","author":"Chao","year":"2005","journal-title":"J. Org. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"1285","DOI":"10.1016\/j.dyepig.2011.09.017","article-title":"Concentration effects on emission of bay-substituted perylene diimide derivatives in a polymer matrix","volume":"92","author":"Miasojedovasa","year":"2012","journal-title":"Dyes Pigm."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"10264","DOI":"10.1021\/ic901379d","article-title":"Building multistate redox-active architectures using metal-complex functionalized perylene bis-imides","volume":"48","author":"Goretzki","year":"2009","journal-title":"Inorg. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"2352","DOI":"10.1016\/j.tetlet.2012.02.107","article-title":"Donor-acceptor perylenediimide-ferrocene conjugates: Synthesis, photophysical, and electrochemical properties","volume":"53","author":"Dhokale","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"5955","DOI":"10.1002\/ejoc.201101051","article-title":"Bay region borylation of perylene bisimides","volume":"30","author":"Dey","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"4724","DOI":"10.1021\/ol2019407","article-title":"Syntheses and properties of 1,6 and 1,7 perylene diimides and tetracarboxylic dianhydrides","volume":"13","author":"Handa","year":"2011","journal-title":"Org. Lett."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"8246","DOI":"10.1039\/c1ob05702b","article-title":"Naphthalene- and perylenediimides with hydroquinones, catechols, boronic esters and imines in the core","volume":"9","author":"Fin","year":"2011","journal-title":"Org. Biomol. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"5427","DOI":"10.1002\/ejoc.201100513","article-title":"Synthesis, electrochemical and optical absorption properties of new perylene-3,4:9,10-bis(dicarboximide) and perylene-3,4:9,10-bis(benzimidazole) derivatives","volume":"28","author":"Perrin","year":"2011","journal-title":"Eur. J. Org. Chem."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"32","DOI":"10.1016\/j.dyepig.2009.11.005","article-title":"Fluorescent macromolecular perylene diimides containing pyrene or indole units in bay positions","volume":"86","year":"2010","journal-title":"Dyes Pigm."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"2402","DOI":"10.1021\/jo062150j","article-title":"Di(alkoxy)- and di(alkylthio)-substituted perylene-3,4;9,10-tetracarboxy diimides with tunable electrochemical and photophysical properties","volume":"72","author":"Zhao","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"298","DOI":"10.1016\/j.dyepig.2011.04.008","article-title":"Synthesis and properties of novel perylenebisimide-cored dendrimers","volume":"91","author":"Ren","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"1094","DOI":"10.1016\/j.tetlet.2011.12.080","article-title":"Facile synthesis of 1-bromo-7-alkoxyl perylene diimide dyes: Toward unsymmetrical functionalizations at the 1,7-positions","volume":"53","author":"Zhang","year":"2012","journal-title":"Tetrahedron Lett."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"23","DOI":"10.1016\/j.dyepig.2010.08.014","article-title":"Synthesis and properties of novel perylenetetracarboxylic diimide derivatives fused with BODIPY units","volume":"89","author":"Feng","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"517","DOI":"10.1016\/j.dyepig.2011.06.023","article-title":"Synthesis, photophysical and electrochemical properties of 1-aminoperylene bisimides","volume":"92","author":"Chen","year":"2011","journal-title":"Dyes Pigm."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"319","DOI":"10.1016\/j.dyepig.2012.09.003","article-title":"1,7-Diaminoperylene bisimides: Synthesis, optical and electrochemical properties","volume":"96","author":"Tsai","year":"2013","journal-title":"Dyes Pigm."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"2107","DOI":"10.1021\/jo052394o","article-title":"Bis(n-octylamino)perylene-3,4:9,10-bis(dicarboximide)s and their radical cations: Synthesis, electrochemistry, and ENDOR spectroscopy","volume":"71","author":"Ahrens","year":"2006","journal-title":"J. Org. Chem."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"7858","DOI":"10.1016\/j.tet.2007.05.096","article-title":"Synthesis and spectroscopic properties of highly water-soluble perylene derivatives","volume":"63","author":"Alvino","year":"2007","journal-title":"Tetrahedron"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1181","DOI":"10.1039\/b717407a","article-title":"Perylene bisimide J-aggregates with absorption maxima in the NIR","volume":"10","author":"Wang","year":"2008","journal-title":"Chem. Commun."},{"key":"ref_81","doi-asserted-by":"crossref","first-page":"778","DOI":"10.1021\/cm1018647","article-title":"1,7- and 1,6-regioisomers of diphenoxy and dipyrrolidinyl substituted perylene diimides: Synthesis, separation, characterization, and comparison of electrochemical and optical properties","volume":"23","author":"Dubey","year":"2011","journal-title":"Chem. Mater."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"7047","DOI":"10.1016\/S0040-4039(99)01468-9","article-title":"3,4:9,10-Perylenebis(dicarboximide) chromophores that function as both electron donors and acceptors","volume":"40","author":"Zhao","year":"1999","journal-title":"Tetrahedron Lett."},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1080\/10610270600902324","article-title":"Perylene diimide dyes aggregates: Optical properties and packing behavior in solution and solid state","volume":"19","author":"Ma","year":"2007","journal-title":"Supramol. Chem."},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"4443","DOI":"10.1016\/j.tetlet.2005.04.137","article-title":"1,6-Disubstituted perylene bisimides: Concise synthesis and characterization as near-infrared fluorescent dyes","volume":"46","author":"Fan","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"1789","DOI":"10.1039\/b009708j","article-title":"Liquid crystalline coronene derivatives","volume":"11","author":"Rohr","year":"2001","journal-title":"J. Mater. Chem."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"5973","DOI":"10.1021\/jo070367n","article-title":"Selective bromination of perylene diimides under mild conditions","volume":"72","author":"Rajasingh","year":"2007","journal-title":"J. Org. Chem."},{"key":"ref_87","doi-asserted-by":"crossref","unstructured":"Lakowicz, J.R. (1999). Principles of Fluorescence Spectroscopy, Plenum. [2nd ed.].","DOI":"10.1007\/978-1-4757-3061-6"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"1279","DOI":"10.1016\/j.cclet.2012.09.009","article-title":"Extensive spectral tuning of the proton transfer emission from green to red via a rational derivatization of salicylideneaniline","volume":"23","author":"Luo","year":"2012","journal-title":"Chin. Chem. Lett."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"145","DOI":"10.1016\/j.cclet.2013.01.011","article-title":"Excited-state charge coupled proton transfer reaction via the dipolar functionality of salicylideneaniline","volume":"24","author":"Fang","year":"2013","journal-title":"Chin. Chem. Lett."}],"container-title":["Materials"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1996-1944\/7\/8\/5488\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T21:14:03Z","timestamp":1760217243000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1996-1944\/7\/8\/5488"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2014,7,25]]},"references-count":89,"journal-issue":{"issue":"8","published-online":{"date-parts":[[2014,8]]}},"alternative-id":["ma7085488"],"URL":"https:\/\/doi.org\/10.3390\/ma7085488","relation":{},"ISSN":["1996-1944"],"issn-type":[{"value":"1996-1944","type":"electronic"}],"subject":[],"published":{"date-parts":[[2014,7,25]]}}}