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

Journal article


Publication Details

Author(s): Luponosov YN, Min J, Solodukhin AN, Bakirov AV, Dmitryakov PV, Shcherbina MA, Peregudova SM, Cherkaev GV, Chvalun SN, Brabec C, Ponomarenko SA
Journal: Journal of Materials Chemistry C
Publication year: 2016
Volume: 4
Journal issue: 29
Pages range: 7061-7076
ISSN: 2050-7526


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.


FAU Authors / FAU Editors

Brabec, Christoph Prof. Dr.
Institute Materials for Electronics and Energy Technology (i-MEET)
Min, Jie
Institute Materials for Electronics and Energy Technology (i-MEET)


Additional Organisation
Exzellenz-Cluster Engineering of Advanced Materials


External institutions with authors

Russian Academy of Sciences / Росси́йская акаде́мия нау́к (RAS)


Research Fields

B Nanoelectronic Materials
Exzellenz-Cluster Engineering of Advanced Materials


How to cite

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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Last updated on 2019-16-03 at 04:08