Jump to main content
Jump to site search

Issue 29, 2016
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Publication details

The article was received on 14 Apr 2016, accepted on 18 Jun 2016 and first published on 20 Jun 2016


Article type: Paper
DOI: 10.1039/C6TC01530A
Citation: J. Mater. Chem. C, 2016,4, 7061-7076
  •   Request permissions

    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

Search articles by author

Spotlight

Advertisements