Synthesis and optical properties of a poly(2′,5′-dioctyloxy-4,4′,4″- terphenylenevinylene) with high content of (Z) vinylene units |
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Authors: | Francesco Babudri Antonio Cardone Gianluca M Farinola Raffaele Tommasi |
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Institution: | a Dipartimento di Chimica, Università di Bari, Via Orabona 4, I-70126 Bari, Italy b CNR ICCOM - Bari, Dipartimento di Chimica, Università di Bari, Via Orabona 4, I-70126 Bari, Italy c Dipartimento di Fisica, Università di Bari, Via Amendola 173, I-70126 Bari, Italy d Dipartimento di Biochimica Medica, Biologia Medica e Fisica Medica, Università di Bari, P.zza G. Cesare 11, I-70124 Bari, Italy |
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Abstract: | Poly(2′,5′-dioctyloxy-4,4′,4″-terphenylenevinylene) with (E) configuration of the vinylene double bonds was prepared by Suzuki-Miyaura polymerization of (E)-4,4′-dibromostilbene and 2,5-dioctyloxy-1,4-benzenediboronic acid. Attempts to extend this simple procedure to the synthesis of the polymer with (Z) configuration, starting from (Z)-4,4′-dibromostilbene, were unsuccessful. However, the use of (Z)-4,4′-diiodostilbene and a careful choice of Pd catalyst and experimental conditions, lead to a material with a >95/<5 (Z)/(E) ratio of vinylene units. The investigation of optical properties of both the (E) and (Z) polymers evidenced that (Z) linkages act as defects which reduce the effective conjugation length in the polymer backbone. |
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Keywords: | Cross-coupling Boron Polymerization PPV Diastereoselectivity |
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