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.
Authors with CRIS profile
Jie Min
Institute Materials for Electronics and Energy Technology (i-MEET) (i-MEET)
Christoph Brabec
Institute Materials for Electronics and Energy Technology (i-MEET) (i-MEET)
Additional Organisation(s)
Involved external institutions
Russian Federation (RU)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://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.
BibTeX: Download