All‐donor poly(arylene‐ethynylene)s containing anthracene and silole‐based units: Synthesis, electronic, and photovoltaic properties. Issue 22 (18th September 2013)

• Record Type: Journal Article
• Authors: Grisorio, Roberto; Suranna, Gian Paolo; Mastrorilli, Piero; Allegretta, Giovanni; Loiudice, Anna; Rizzo, Aurora; Gigli, Giuseppe; Manoli, Kyriaki; Magliulo, Maria; Torsi, Luisa
• Is Part Of: Journal of polymer science. Volume 51:Issue 22(2013:Nov.)
• Page Start: 4860
• Page End: 4872
• Publication Date: 2013-09-18
• Subjects: 547
• DOI: 10.1002/pola.26914
• Languages: English
• ISSNs: 0887-624X

Abstract

<abstract abstract-type="main"> <title>ABSTRACT</title> <p>The manuscript deals with the synthesis and properties of four new all‐donor alternating poly(arylene‐ethynylene)s <bold>DBSA</bold>, <bold>DBSTA</bold>, <bold>DTSA</bold>, and <bold>DTSTA</bold>. The polymers have been obtained by a Sonogashira cross‐coupling of 9, 10‐diethynyl‐anthracene with the dibromo‐derivatives of 9, 9‐dioctyl‐dibenzosilole (<bold>DBSA</bold>), 2, 7‐dithienyl‐9, 9‐dioctyl‐dibenzosilole (<bold>DBSTA</bold>), 4, 4‐dioctyl‐dithienosilole (<bold>DTSA</bold>), or 2, 6‐dithienyl‐9, 9‐dioctyl‐dithienosilole (<bold>DTSTA</bold>). The polymers exhibited absorption profiles and frontier orbital energies strongly dependent on their primary structure. Density functional theory calculations confirmed experimental observations and provided an insight into the electronic structure of the macromolecules. In particular, the effects exerted by the thiophene units in <bold>DBSTA</bold> and <bold>DTSTA</bold> on the optical properties of the corresponding polymers could be rationalized with respect to <bold>DBSA</bold> and <bold>DTSA</bold>. Preliminary photovoltaic measurements have established that the performance of <bold>DTSA</bold> is among the highest reported for an all‐donor polymer. Moreover, UV irradiation of <bold>DTSA</bold> films under air evidenced a remarkable photostability of this material, providing further evidence that ethynylene‐containing electron‐rich systems are promising donors for organic solar cells applications. © 2013 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. <bold>2013</bold>, <italic>51</italic>, 4860–4872</p> </abstract>