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Carbazole-Based Ladder-Type Heptacylic Arene with Aliphatic Side Chains Leading to Enhanced Efficiency of Organic Photovoltaics

Authors :
Jhong Sian Wu
Ping I. Shih
Wei Shun Kao
Yen-Ju Cheng
Chain-Shu Hsu
Pei Chi Jwo
Chih Yu Chang
Source :
Chemistry of Materials. 23:2361-2369
Publication Year :
2011
Publisher :
American Chemical Society (ACS), 2011.

Abstract

By utilizing Friedel−Crafts cyclization, we have successfully designed and synthesized a ladder-type heptacyclic carbazole-dicyclopentathiophene (CDCT-C8) unit in which two outer thiophene subunits are covalently fastened to the central 2,7-carbazole core. The nitrogen-directing effect of the carbazole unit facilitates the intramolecular cyclization and thereby suppresses the acid-induced dehydration, allowing us to incorporate two octyl side chains on the cyclopentadiene rings in good chemical yield. The distannyl-CDCT-C8 building block was copolymerized with benzothiadiazole (BT), dithienylbenzothiadiazole (DTBT), dithienyldiketopyrrolopyrrole (DTDPP) and quinoxaline (QX) units by Stille polymerization to afford four alternating donor−acceptor copolymers, PCDCTBT-C8, PCDCTDTBT-C8, PCDCTDTDPP-C8 and PCDCTQX-C8, respectively. The device based on the PCDCTBT-C8:PC71BM (1:3 in wt%) blend exhibited a Voc of 0.74 V, a Jsc of 10.3 mA/cm2, a FF of 60%, delivering an impressive PCE of 4.6%. This value represents...

Details

ISSN :
15205002 and 08974756
Volume :
23
Database :
OpenAIRE
Journal :
Chemistry of Materials
Accession number :
edsair.doi...........cae6d7f11b44587f6f36a103d8be99c3
Full Text :
https://doi.org/10.1021/cm200041v