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Push–pull thiophene chromophores for electro-optic applications: from 1D linear to β-branched structures

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Abstract

We report the synthesis and characterization of a novel series of push–pull chromophores bearing 1D linear and β-branched thiophenes as π-conjugated spacers between a 2,2,4,7-tetramethyl-1,2,3,4-tetrahydroquinoline electron donor unit and dicyano- and tricyanovinylene electron acceptor groups. The effect of the introduction of β-thiophenes on the linear and nonlinear (NLO) optical properties as well as electrochemical and thermal data is studied in detail by performing a comparative study between the branched and 1D linear systems. In addition, a parallel DFT computational study is used to evaluate structure–property relationships. The non-linear optical behavior of the molecules both in solution and in solid state as electro-optic (EO) films using a guest–host approach shows very promising performance for electro-optic applications with high molecular first hyperpolarizabilities (μβ) of 4840 × 10−48 esu and electro-optic coefficients r33 reaching 650 pm V−1. One highlight is that the electro-optic films of the β-branched chromophores are superior in terms of thermal stability in device operation as measured by a transmissive modified reflective Teng-Man method. This work provides guidelines for the design of improved electro-optic materials including β-branched chromophores which could be useful for practical EO applications, where both enhanced β and r33 values together with chemical and thermal stability are necessary.

Graphical abstract: Push–pull thiophene chromophores for electro-optic applications: from 1D linear to β-branched structures

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Supplementary files

Article information


Submitted
16 Oct 2019
Accepted
30 Dec 2019
First published
02 Jan 2020

Phys. Chem. Chem. Phys., 2020, Advance Article
Article type
Paper

Push–pull thiophene chromophores for electro-optic applications: from 1D linear to β-branched structures

C. Rothe, D. Neusser, N. Hoppe, K. Dirnberger, W. Vogel, S. Gámez-Valenzuela, J. T. López Navarrete, B. Villacampa, M. Berroth, M. C. Ruiz Delgado and S. Ludwigs, Phys. Chem. Chem. Phys., 2020, Advance Article , DOI: 10.1039/C9CP05640H

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