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

Luponosov YN, Min J, Solodukhin AN, Bakirov AV, Dmitryakov PV, Shcherbina MA, Peregudova SM, Cherkaev GV, Chvalun SN, Brabec C, Ponomarenko SA (2016)


Publication Type: Journal article

Publication year: 2016

Journal

Book Volume: 4

Pages Range: 7061-7076

Journal Issue: 29

DOI: 10.1039/c6tc01530a

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 \textgreekp-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 \textgreekp-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.

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APA:

Luponosov, Y.N., Min, J., Solodukhin, A.N., Bakirov, A.V., Dmitryakov, P.V., Shcherbina, M.A.,... Ponomarenko, S.A. (2016). Star-shaped D-π-A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties. Journal of Materials Chemistry C, 4(29), 7061-7076. https://dx.doi.org/10.1039/c6tc01530a

MLA:

Luponosov, Yuriy N., et al. "Star-shaped D-π-A oligothiophenes with a tris(2-methoxyphenyl)amine core and alkyldicyanovinyl groups: synthesis and physical and photovoltaic properties." Journal of Materials Chemistry C 4.29 (2016): 7061-7076.

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