Issue 36, 2016

New anisopleural spindle-like nonlinear optic (NLO) chromophores with a D–D′–π–A′–A or D–A′–π–D′–A structure: interesting optical behavior and DFT calculation results

Abstract

A new series of anisopleural spindle-like chromophores which have both auxiliary donors and acceptors on their conjugated bridge has been designed and synthesized for the first time. The auxiliary donors and acceptors were introduced close to the donors and acceptors respectively and formed D–D′–π–A′–A structure chromophores termed S-chromophores. The opposite D–A′–π–D′–A structure chromophores are termed F-chromophores. The structure–properties relationship based on these anisopleural spindle-like chromophores has been investigated via1H-NMR, UV-vis characterization and DFT theoretical calculations. S-Chromophores displayed varied chemical shifts of the double-bond proton and a red-shifted maximum absorption wavelength (λmax) as well as a larger absorption intensity (ε) compared to the F-chromophores, indicating that the intermolecular charge transfer has been influenced by the structures. Moreover, the red-shifted λmax and larger ε indicate a more efficient intermolecular charge transfer which should in turn lead to an increased hyperpolarizability (β) for a given class structure of chromophores. The theoretical calculation β values of the S-chromophores showing an increase further rationalize the experimental results. In this way, the structure–properties relationship has been investigated and established.

Graphical abstract: New anisopleural spindle-like nonlinear optic (NLO) chromophores with a D–D′–π–A′–A or D–A′–π–D′–A structure: interesting optical behavior and DFT calculation results

Article information

Article type
Paper
Submitted
16 may 2016
Accepted
08 avq 2016
First published
09 avq 2016

J. Mater. Chem. C, 2016,4, 8392-8398

New anisopleural spindle-like nonlinear optic (NLO) chromophores with a D–D′–π–A′–A or D–A′–π–D′–A structure: interesting optical behavior and DFT calculation results

C. Li, M. Li, Y. Li, Z. Shi, Z. Li, X. Wang, J. Sun, J. Sun, D. Zhang and Z. Cui, J. Mater. Chem. C, 2016, 4, 8392 DOI: 10.1039/C6TC02016J

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