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Synthesis and optical properties of biphenylene ethynylene co-polymers and their model compounds

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Abstract

A new series of biphenylene ethynylene co-polymers, poly(2,5-dialkoxy-4-phenyleneethynylene-4,4-biphenyleneethynylene)s of the general formula [-C ≡C-4-C6H4-C6H4-4-C ≡C-C6H2(2,5-OR)2-]n (R = C4H9 P1, C8H17 P2) has been synthesized using a palladium/copper catalyzed coupling reaction between HC ≡C-4-C6H4-C6H4-4-C ≡C-H and IC6H2(2,5-OR)2I. The new co-polymer [-C ≡C-C6H2(2,5-OC8H17)2-C ≡C-C6H2(2,5-OC4H9)2-]n P5 has also been formed where different alkoxy substituents are present on alternate arene rings in the same polymer backbone. All the polymers were characterized by IR, 1H and 13C NMR spectroscopy and by GPC. The model compounds C6H5-4-C6H4-C≡C-C6H2(2,5-OR)2-4-C6H4-C6H5 (R = C4H9 M1, C8H17 M2) have also been prepared by the reaction between C6H5-4-C6H4-C≡CH and IC6H2(2,5-OR)2I. Single crystal X-ray structures of M1, M2 and Me3Si-C≡C-4-C6H4-C6H4-4-C≡C-SiMe3 were determined with a view to obtain a better understanding of the molecular and intermolecular interactions in the solid state which has been used to explain the optical properties of the polymers derived from them. The absorption and photoluminescence spectra of the polymers, P1, P2 and P5 showed that the lowest energy band is blue shifted due to the introduction of biphenylene fragments into the alkoxy substituted poly(ethynylenephenylene)s.

Synthesis, structural characterization and optical spectroscopy of poly(2,5-dialkoxy-1,4-phenylene-4-4-biphenyleneethynylene)s, [-C≡C-4-C6H4-C6H4-4-C≡C-C6H4(2,5-OR)2-]n (R = C4H9, C8H17) and their model compounds are reported.

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Acknowledgements

We are grateful to the Leverhulme Trust and the Royal Society, UK; and Higher Education Quality Enhancement Project (HEQEP), UGC, Bangladesh for financial support (to M. Y.), Shahjalal University for study leave (to M. Y.), and the EPSRC for funding to purchase the X-ray diffractometer. The EPSRC sponsored polymer molecular weight determination service run by RAPRA is gratefully acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, Shahjalal University of Science and Technology, Sylhet, 3114, Bangladesh

    OKHIL K NAG, KAZI M ANIS-UL-HAQUE, DIPEN DEBNATH, ROCKSHANA BEGUM & MUHAMMAD YOUNUS

  2. Department of Physics, Shahjalal University of Science and Technology, Sylhet, 3114, Bangladesh

    NAZIA CHAWDHURY

  3. Department of Chemistry, University of Bath, Bath, BA2 7AY, UK

    GABRIELE KOCIOK-KÖHN & PAUL R RAITHBY

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  1. OKHIL K NAG
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  2. KAZI M ANIS-UL-HAQUE
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Correspondence to MUHAMMAD YOUNUS.

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Supplementary Information

The 13C NMR spectrum of C6H5-4-C6H4-C≡C-C6H4(2,5-OC8H17)2-C6H4-4-C6H5 M2; and crystal data, data collection and structure refinement for M1, M2 and Me3SiC≡C(C6H4)2C≡CSiMe3 are available from the Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif or from the Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: + 44 1223 336 033; or e-mail: deposit@ccdc.cam.ac.uk. The CCDC reference numbers for the three crystal structures are 997486-997488. Supplementary information is also available at www.ias.ac.in/chemsci.

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NAG, O.K., ANIS-UL-HAQUE, K.M., DEBNATH, D. et al. Synthesis and optical properties of biphenylene ethynylene co-polymers and their model compounds. J Chem Sci 127, 365–374 (2015). https://doi.org/10.1007/s12039-015-0789-y

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