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Updated: May 27, 2026

Time-resolved Photophysical Characterization of Triplet-harvesting Organic Compounds at an Oxygen-free Environment Using an iCCD Camera
Published on: December 27, 2018
N,N'-Dicyanoquinone diimide-derived donor-acceptor chromophores: conformational analysis and optoelectronic
Melanie Chiu1, Bernhard Jaun, Marten T R Beels
1Laboratorium für Organische Chemie, ETH Zürich , Hönggerberg, 8093 Zürich, Switzerland.
Abstract:
A formal [2 + 2] cycloaddition-cycloreversion (CA-CR) between N,N'-dicyanoquinone diimides (DCNQIs) and electron-rich alkynes was explored, providing a new class of π-conjugated donor-acceptor chromophores. These DCNQI adducts exist in the solid state as single diastereoisomers, but as two interconverting diastereoisomers in solution. Solid- and solution-state evidence for intramolecular charge transfer (CT) was obtained; additionally, the DCNQI adducts exhibit positive solvatochromism and significant solution-state third-order polarizabilities.
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The simplest example of a diene is 1,3-butadiene, an acyclic conjugated π system. At room temperature, the molecule exists as a mixture of s-cis and s-trans conformers by virtue of rotation around the carbon–carbon single bond. Although the s-trans isomer is more stable, the...