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Synthesis of Conjugated Tetrathiafulvalene (TTF)‐π‐Acceptor Molecules − Intramolecular Charge Transfer and Nonlinear Optical Properties
Author(s) -
Bryce Martin R.,
Green Andrew,
Moore Adrian J.,
Perepichka Dmitrii F.,
Batsanov Andrei S.,
Howard Judith A.K.,
LedouxRak Isabelle,
González Mar,
Martín Nazario,
Segura José L.,
Garín Javier,
Orduna Jesús,
Alcalá Rafael,
Villacampa Belén
Publication year - 2001
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200105)2001:10<1927::aid-ejoc1927>3.0.co;2-4
Subject(s) - tetrathiafulvalene , chemistry , intramolecular force , moiety , conjugated system , acceptor , photochemistry , chromophore , molecule , electron acceptor , ab initio , crystallography , stereochemistry , organic chemistry , physics , condensed matter physics , polymer
We have synthesised new conjugated donor‐π‐acceptor (D‐π‐A) chromophores 7 , 9 , and 12 − 15 in which monosubstituted tetrathiafulvalene (TTF) and trimethyl‐TTF units are the donor moieties, connected by ethylenic bridges to electron‐deficient benzene derivatives as the acceptor moieties. These compounds display a broad intramolecular charge transfer (ICT) band in their solution UV/Vis spectra at λ max = ca. 500 nm. The second order nonlinear optical (NLO) properties of these derivatives have been studied using the EFISH technique and calculated by semiempirical and ab initio theoretical methods. The effect of methyl substituents in the TTF moiety and the nature of the conjugated bridge are discussed. Analysis of the bond lengths obtained by an X‐ray diffraction study of compound 9 reveal ICT in the solid state.