Synthesis and Characterization of Star-Shaped Donor-Acceptor-Donor Structures

• Published in: European journal of organic chemistry Vol. 2013; no. 22; pp. 4761 - 4769
• Main Authors: Pelz, Simon, Zhang, Jinming, Kanelidis, Ioannis, Klink, Dennis, Hyzak, Lukas, Wulf, Volker, Schmitz, Oliver J., Gasse, Jan-Christoph, Frahm, Ronald, Pütz, Andreas, Colsmann, Alexander, Lemmer, Uli, Holder, Elisabeth
• Format: Journal Article
• Language: English
• Published: Weinheim WILEY-VCH Verlag 01.08.2013; WILEY‐VCH Verlag; Wiley; Wiley Subscription Services, Inc
• Subjects: Chemistry; Chemistry, Organic; Cross-cou­pling; Heterocycles; Materials science; NMR spectroscopy; Physical Sciences; Polymers; Science & Technology; UV/Vis spectroscopy; Heterocycles; UV; POLYMERS; Materials science; COPOLYMERS; OLIGOTHIOPHENES; COMPOSITES; RED; Cross-coupling; Vis spectroscopy; ABSORPTION; NMR spectroscopy; FLUORENE
• ISSN: 1434-193X; 1099-0690
• DOI: 10.1002/ejoc.201300357

A Sonogashira coupling reaction led to star‐shaped 1,3,5‐tris({5‐[7‐(thiophen‐2‐yl)benzo[c][1,2,5]thiadiazol‐4‐yl]thiophen‐2‐yl}ethynyl)benzene derivatives. The star‐shaped molecules were optically analyzed, and – depending on their substitution pattern – they displayed bathochromically shifted absorptions, which were compared to their nonlinked arm precursors. The materials displayed a highly interesting morphology in bulk when blended with [6,6]‐phenyl‐C61‐butyric acid methyl ester (PCBM). One derivative formed columnar structures and revealed prospective use in photodiodes. Palladium‐catalyzed cross‐coupling reactions led to different star‐shaped derivatives with donor–acceptor–donor segments. Upon annealing, one derivative formed columnar structures and revealed a prospective use in ternary photodiodes.