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

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 abso...

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Veröffentlicht in:European journal of organic chemistry 2013-08, Vol.2013 (22), p.4761-4769
Hauptverfasser: 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
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Sprache:eng
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Zusammenfassung: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.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201300357