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Issue 29, 2016
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Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

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Abstract

Synthesis of a series of star-shaped oligomers having a novel electron donating tris(2-methoxyphenyl)amine (m-TPA) core, which is linked through a bithiophene or terthiophene π-bridge with electron-deficient alkyldicyanovinyl (alkyl-DCV) groups, is described. A comprehensive study of the oligomers revealed significant dependence of their physical properties, including absorption, molecular frontier energy levels, crystal packing, and melting and glass transition temperatures, upon the chemical structure. A comparison of their photophysical properties to the nearest analog having the common dicyanovinyl (DCV) groups demonstrated a number of benefits to use alkyl-DCV units for the design of donor–acceptor small molecules: higher solubility, increased electrochemical stability, better photovoltaic performance, and possibility to control the relative physical and photovoltaic properties by a simple adjustment of alkyl and π-bridge lengths. Modification of the well-known triphenylamine (TPA) core in the star-shaped oligomers by methoxy groups increases not only solubility, but also crystallinity of the oligomers, whereas their photovoltaic performance stays on a similar level as their analogs with a TPA core. The study demonstrates that these design strategies represent interesting and simple tools for the effective modulation of properties of star-shaped molecules.

Graphical abstract: Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

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Supplementary files

Article information


Submitted
14 Apr 2016
Accepted
18 Jun 2016
First published
20 Jun 2016

J. Mater. Chem. C, 2016,4, 7061-7076
Article type
Paper

Star-shaped D–π–A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties

Y. N. Luponosov, J. Min, A. N. Solodukhin, A. V. Bakirov, P. V. Dmitryakov, M. A. Shcherbina, S. M. Peregudova, G. V. Cherkaev, S. N. Chvalun, C. J. Brabec and S. A. Ponomarenko, J. Mater. Chem. C, 2016, 4, 7061
DOI: 10.1039/C6TC01530A

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