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Symmetrical and Nonsymmetrical Chromophores with Tröger’s Base Skeleton: Chiroptical, Linear, and Quadratic Nonlinear Optical Properties—A Joint Theoretical and Experimental Study
Author(s) -
Sergeyev Sergey,
Didier Delphine,
Boitsov Vitaly,
Teshome Ayele,
Asselberghs Inge,
Clays Koen,
Vande Velde Christophe M. L.,
Plaquet Aurélie,
Champagne Benoît
Publication year - 2010
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.201000216
Subject(s) - chromophore , nonlinear optical , acceptor , materials science , chemistry , nonlinear system , photochemistry , physics , quantum mechanics
We report on the novel chiral push–pull chromophores derived from 6 H ,12 H ‐5,11‐methanodibenzo[ b , f ][1,5]diazocine (Tröger’s base skeleton). The synthesis of symmetrical chromophores featuring two identical acceptors, as well as the synthesis of unsymmetrical chromophores featuring only one acceptor is given. Symmetrical chromophores were prepared in the enantiomerically pure form and their chiroptical properties were investigated. Second‐order nonlinear optical (NLO) properties of new chromophores were investigated with the aid of hyper‐Rayleigh scattering (HRS). The detailed theoretical analysis of the second‐order NLO properties of the chromophores was also undertaken. The joint theoretical and experimental studies of chromophores derived from Tröger’s base skeleton, in comparison with benchmark chromophores featuring a dimethylamino group as the donor, provided insight into the relationship between the structure of the new chromophores and their NLO properties.