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A novel unsymmetrically substituted chiral amphiphilic perylene diimide: Synthesis, photophysical and electrochemical properties both in solution and solid state

Paper ID Volume ID Publish Year Pages File Format Full-Text
26218 43940 2016 10 PDF Available
Title
A novel unsymmetrically substituted chiral amphiphilic perylene diimide: Synthesis, photophysical and electrochemical properties both in solution and solid state
Abstract

•We synthesized two chiral amphiphilic perylene dye using lipophilic moiety (+)-dehydroabietylamine and hydrophilic substituent l-lysine.•Dehydroabietylamine was specifically selected in order to minimize stacking properties and maximize solubility.•Intermolecular interactions kept under control via l-lysine moiety•The solid state red color emission centered at a wavelength of 632 nm for 1 is promising for further organic light emitting diodes technology.•The concentration dependent emission color observed for 1 and 3 offer challenges in the design of different photonic systems.

A novel unsymmetrically substituted chiral amphiphilic perylene diimide with two different quaternary stereocenters was synthesized. For comparison, symmetrically substituted chiral perylene diimide containing the same quaternary stereocenters was prepared. The dehydroabietylamine was specifically selected in order to minimize stacking properties and maximize solubility. Intermolecular interactions kept under control via l-lysine moiety. The specific optical rotation ([α]D20,alpha) of symmetrically and unsymmetrically substituted perylene dyes measured at 20 °C in chloroform as −105 and +200, respectively. Both of the compounds have excellent solubility in a wide range of organic solvents and symmetrically substituted chiral perylene diimide gives strong fluorescence emission (632 nm) in solid state. Concentration dependent self-aggregation of both compounds results in tunability of fluorescence emission. Compounds are thermally, photophysically and electrochemically stable.

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Keywords
Unsymmetrically substituted; Chiral,hydrogen bonding; Excimer emission; Perylene
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A novel unsymmetrically substituted chiral amphiphilic perylene diimide: Synthesis, photophysical and electrochemical properties both in solution and solid state
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Publisher
Database: Elsevier - ScienceDirect
Journal: Journal of Photochemistry and Photobiology A: Chemistry - Volume 318, 1 March 2016, Pages 104–113
Authors
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Subjects
Physical Sciences and Engineering Chemical Engineering Bioengineering
Get Full-Text Now
Don't Miss Today's Special Offer
Price was $35.95
You save - $31
Price after discount Only $4.95
100% Money Back Guarantee
Full-text PDF Download
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Any Questions? feel free to contact us