Preparation and Characterization of Regioisomerically Pure 1,7-Disubstituted Perylene Bisimide Dyes
Top Cited Papers
- 19 October 2004
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 69 (23) , 7933-7939
- https://doi.org/10.1021/jo048880d
Abstract
A detailed study on bromination and subsequent imidization of perylene bisanhydride with cyclohexylamine is reported. The present results reveal that previously reported 1,7-difunctionalized perylene bisimides are presumably contaminated with the respective 1,6 regioisomers. N,N‘-Dicyclohexyl-1,7-dibromoperylene bisimide 1,7-3 is obtained for the first time in isomerically pure form, and its structure is unequivocally confirmed by X-ray analysis. By using regioisomerically pure 1,7-dibromoperylene bisimide 1,7-3, 1,7-dipyrrolidinylperylene bisimides 4a−c and 1,7-dipyrrolidinylperylene bisanhydride 5 as well as the unsymmetrically difunctionalized 1-bromo-7-pyrrolidinyl- and 1-cyano-7-pyrrolidinylperylene bisimides 7 and 8 are synthesized in good yield.Keywords
This publication has 30 references indexed in Scilit:
- Microwave Driven Bray–Liebhafsky Oscillatory ReactionChemphyschem, 2004
- Electroluminescent Diodes from Complementary Discotic BenzoperylenesChemphyschem, 2003
- Photoinduced Electron Transfer in a Mesogenic Donor–Acceptor–Donor SystemChemistry – A European Journal, 2002
- Hybrid Photorefractive Material Composed of Layered Conjugated Polymer and Dye-Doped Liquid Crystal FilmsChemistry of Materials, 2002
- Biomimetic Electron Transfer Using Low Energy Excited States: A Green Perylene-Based Analogue of ChlorophyllaThe Journal of Physical Chemistry B, 2002
- Liquid crystalline coronene derivativesJournal of Materials Chemistry, 2001
- Liquid Crystalline Perylene Diimides: Architecture and Charge Carrier MobilitiesJournal of the American Chemical Society, 2000
- Lasing action in a family of perylene derivatives: singlet absorption and emission spectra, triplet absorption and oxygen quenching constants, and molecular mechanics and semiempirical molecular orbital calculationsThe Journal of Physical Chemistry, 1992
- Crystallochromy as a solid-state effect: correlation of molecular conformation, crystal packing and colour in perylene-3,4:9,10-bis(dicarboximide) pigmentsActa crystallographica Section B, Structural science, crystal engineering and materials, 1989
- New perylene and violanthrone dyestuffs for fluorescent collectorsDyes and Pigments, 1989