{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,29]],"date-time":"2026-09-29T13:54:06Z","timestamp":1790690046452,"version":"4.1.0"},"reference-count":69,"publisher":"MDPI AG","issue":"12","license":[{"start":{"date-parts":[[2014,12,8]],"date-time":"2014-12-08T00:00:00Z","timestamp":1417996800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>Three dialkylamino-substituted perylene tetracarboxylic dianhydrides with different n-alkyl chain lengths (n = 6, 12 or 18), 1a\u20131c, were synthesized under mild conditions in high yields and were characterized by 1H NMR, 13C NMR and high resolution mass spectroscopy. Their optical and electrochemical properties were measured using UV-Vis and emission spectroscopic techniques, as well as cyclic voltammetry (CV). This is the first time that the structures and the properties of monoamino-substituted perylene tetracarboxylic dianhydrides have been reported. These molecules show a deep green color in both solution and the solid state and are soluble in most organic solvents. They all show a unique charge transfer emission in the near-infrared region, and the associated peaks exhibit solvatochromism. The dipole moments of the compounds have been estimated using the Lippert-Mataga equation, and upon excitation, they show slightly larger dipole moment changes than those of corresponding perylene diimides, 2a\u20132c. Additionally, Compounds 1a\u20131c undergo two quasi-reversible one-electron oxidations  and two quasi-reversible one-electron reductions in dichloromethane at modest potentials. Complementary density functional theory calculations performed on these chromophores are reported in order to gain more insight into their molecular structures and optical properties.<\/jats:p>","DOI":"10.3390\/ijms151222642","type":"journal-article","created":{"date-parts":[[2014,12,8]],"date-time":"2014-12-08T11:15:56Z","timestamp":1418037356000},"page":"22642-22660","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Highly Soluble Monoamino-Substituted Perylene Tetracarboxylic Dianhydrides: Synthesis,  Optical and Electrochemical Properties"],"prefix":"10.3390","volume":"15","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-2193-688X","authenticated-orcid":false,"given":"Kew-Yu","family":"Chen","sequence":"first","affiliation":[{"name":"Department of Chemical Engineering, Feng Chia University, Taichung 40724, Taiwan"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Che-Wei","family":"Chang","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":[[2014,12,8]]},"reference":[{"key":"ref_1","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 Pigment."},{"key":"ref_2","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 Pigment."},{"key":"ref_3","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. 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