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Origin of Intense Intramolecular Charge‐Transfer Interactions in Nonplanar Push–Pull Chromophores
Author(s) -
Kato Shinichiro,
Kivala Milan,
Schweizer W. Bernd,
Boudon Corinne,
Gisselbrecht JeanPaul,
Diederich François
Publication year - 2009
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200901630
Subject(s) - tetracyanoethylene , chromophore , intramolecular force , tetrathiafulvalene , tetracyanoquinodimethane , ferrocene , charge (physics) , electron transfer , electron , chemistry , electrochemistry , photochemistry , materials science , stereochemistry , physics , molecule , organic chemistry , quantum mechanics , electrode
Nonplanar push–pull chromophores with tetrathiafulvalene and ferrocene donors (see picture) were prepared by formal [2+2] cycloadditions between electron‐rich alkynes and tetracyanoethylene (TCNE) or 7,7,8,8‐tetracyanoquinodimethane (TCNQ). X‐ray crystallographic studies, complemented by UV/Vis and electrochemical measurements, provide clear insight into the remarkably strong intramolecular charge‐transfer interactions in these chromophores, despite their pronounced nonplanarity.