Premium
ThDione: A Powerful Electron‐Withdrawing Moiety for Push–Pull Molecules
Author(s) -
Novotná Eva,
Kityk Iwan V.,
Pytela Oldřich,
Bureš Filip,
Ludwig Miroslav,
Klikar Milan,
Ozga Katarzyna,
Jedryka Jaroslaw
Publication year - 2020
Publication title -
chempluschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.801
H-Index - 61
ISSN - 2192-6506
DOI - 10.1002/cplu.202000395
Subject(s) - moiety , intramolecular force , ferrocene , chromophore , thiophene , acceptor , homo/lumo , molecule , photochemistry , phenothiazine , polar effect , electron transfer , chemistry , materials science , electrochemistry , stereochemistry , organic chemistry , electrode , medicine , physics , pharmacology , condensed matter physics
Abstract A series of new push–pull chromophores based on a combined cyclopenta[ c ]thiophene‐4,6‐dione (ThDione) acceptor, N , N ‐dimethylaniline, N ‐piperidinylthiophene or ferrocene donors, and ethylene or buta‐1,3‐dienylene π‐linkers has been designed and synthesized. Utilizing one or two ThDione acceptors afforded linear or branched push–pull molecules. Experimental and theoretical study of their fundamental properties revealed thermal robustness up to 260 °C, a electrochemical/optical HOMO–LUMO gap that is tunable within the range of 1.47–2.19/1.99–2.39 eV, and thorough elucidation of structure–property relationships. Compared to currently available portfolio of heterocyclic electron‐withdrawing units, ThDione proved to be a powerful and versatile acceptor unit. It imparts significant intramolecular charge transfer and polarizes the π‐system, which results in enhanced (non)linear optical response.