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1,4‐Phenylene and 2,5‐Thienylene π‐Linkers in Charge‐Transfer Chromophores
Author(s) -
Kulhánek Jiří,
Bureš Filip,
Opršal Jakub,
Kuznik Wojciech,
Mikysek Tomáš,
Růžička Aleš
Publication year - 2013
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201300063
Subject(s) - chemistry , chromophore , phenylene , bathochromic shift , intramolecular force , moiety , photochemistry , molecular wire , ferrocene , linker , thiophene , molecule , electrochemistry , stereochemistry , organic chemistry , electrode , quantum mechanics , fluorescence , polymer , computer science , operating system , physics
Fifteen model charge‐transfer chromophores with ferrocene donors, NO 2 acceptors, and 1,4‐phenylene and 2,5‐thienylene π‐linkers were synthesized and their properties investigated by X‐ray analysis, electrochemistry, absorption spectra, and DFT calculations. Structure–property relationships were further evaluated to answer the question of suitability of the π‐linkers in the construction of chromophore backbone. Gradual replacement of 1,4‐phenylene with 2,5‐thienylene and π‐linker extension resulted in a lower HOMO–LUMO gap, a bathochromic shift of both charge‐transfer bands, and overall planarization of the molecule. Hence, thiophene, when incorporated into a chromophore backbone, is a more polarizable moiety that allows very efficient intramolecular charge transfer.