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Updated: Dec 27, 2025

Synthesis of pH Dependent Pyrazole, Imidazole, and Isoindolone Dipyrrinone Fluorophores using a Claisen-Schmidt Condensation Approach
Published on: June 10, 2021
Synthesis and Characterization of Isoindigo-Based Push-Pull Chromophores
Yogajivan Rout1, Vivek Chauhan1, Rajneesh Misra1
1Department of Chemistry, Indian Institute of Technology, Indore 453552, India.
Abstract:
Symmetrical and unsymmetrical chromophores of isoindigo 3-7 were designed and synthesized, in which isoindigo was used as the central unit (electron acceptor unit A), triphenylamine as the end capping unit (electron donor group D), 1,1,4,4-tetracyanobutadiene (TCBD, A') and cyclohexa-2,5-diene-1,4-diylidene-expanded TCBD (A″) as the acceptor unit. The effects of multiacceptor units on photophysical, electrochemical, and computational studies were investigated. The photophysical properties of isoindigo 6 and 7 exhibit a strong intramolecular charge transfer (ICT) absorption band in the near IR region. The isoindigo 4-7 shows multi-redox waves with a low electrochemical band gap, which signifies the tuning of highest occupied molecular orbital-lowest unoccupied molecular orbital energy levels and enhance the π-conjugation. The computational studies demonstrate that there is a good agreement with experimental data. The molecular design and synthesis of isoindigo 4-7 gives a new avenue for the development of building blocks in organic electronics.
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