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Synthesis, characterization and photo – switching properties of azobenzene mesogen containing poly (ether - ester) s from cashew nut shell liquid

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Abstract

Poly(ether - ester)s containing azobenzene mesogen were prepared from cardanol, a natural renewable resource and waste of the cashew industry. The azobenzene group containing cardanol (HPPP) was synthesized by the coupling reaction between diazotized aminophenol and cardanol. Further, it was alkylated with 3 – bromopropanol by Williamson’s etherification process to 3- {4- [4-(3- hydroxy propoxy) phenylazo] -3- pentadecyl phenoxy} propan – 1 – ol(3-HPPP). This dihydroxy compound was characterized by CHN analyzer, UV and 1H and 13C - NMR spectroscopies. A series of azobenzene mesogen containing poly (ether – ester)s were synthesized from 3-HPPP and various aliphatic and aromatic diacid chlorides by solution polycondensation technique. The molecular structure of the monomer and polymers was confirmed by FTIR, 1H and 13C - NMR spectral analyses. These polymers were studied for their thermal stability and photochemical properties. Thermal properties were evaluated by TGA and DSC. Hot-stage optical polarizing microscopy (HOPM) study showed that most of the polymers exhibit smectic and highly ordered band structure. The photo-switching property of azopolymers was investigated using UV – Vis spectroscopy and noticed that trans to cis isomerization occurs within 35 s in DMF, whereas reverse process takes place in 4 h in DMF solvent.

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Acknowledgements

The authors gratefully acknowledge the Principal and Management, PSG College of Technology, Coimbatore for providing the necessary facilities. This work was supported by the University Grants Commission (UGC), India for financial assistance [Grant No. F.No.39-804/2010 (SR)]. Sincere thanks are also due to SAIF, Indian Institute of Science, Bangalore for NMR spectral studies and STIC - Cochin University for TGA analysis.

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  1. Polymer Research Laboratory, Chemistry Division, Department of Applied Science, PSG College of Technology, Coimbatore, 641004, India

    Natarajan Moorthy & Salem Chandrasekaran Murugavel

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  1. Natarajan Moorthy
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  2. Salem Chandrasekaran Murugavel
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Correspondence to Salem Chandrasekaran Murugavel.

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Moorthy, N., Murugavel, S.C. Synthesis, characterization and photo – switching properties of azobenzene mesogen containing poly (ether - ester) s from cashew nut shell liquid. J Polym Res 25, 78 (2018). https://doi.org/10.1007/s10965-018-1449-y

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