Synthesis and Characterization of New Conjugated Polymers Based on Furan Ring from D-fructose and Their Photoluminescence and Thermal Properties

Wael Sadiq Hanoon; Widad Salih Hanoosh; Raed Kadim Zaidan

doi:10.22146/ijc.104800

Synthesis and Characterization of New Conjugated Polymers Based on Furan Ring from D-fructose and Their Photoluminescence and Thermal Properties

https://doi.org/10.22146/ijc.104800

Wael Sadiq Hanoon^(1*), Widad Salih Hanoosh⁽²⁾, Raed Kadim Zaidan⁽³⁾

(1) Department of Chemistry, University of Basrah, Basrah 61004, Iraq
(2) Department of Chemistry, University of Basrah, Basrah 61004, Iraq
(3) Department of Chemistry, University of Basrah, Basrah 61004, Iraq
(*) Corresponding Author

Abstract

Conjugated polymers are one of the most essential branches of polymer science. Most conjugated polymers have a small band gap energy between the ground state and excited state, making them fluorescent materials useful for use as light emitting diodes (LED), sensors, digital screens, and others. We synthesized dialdehyde compound (F1) with good yield and high quality from a natural source (D-fructose) and characterized by proton nuclear magnetic resonance (¹H-NMR), carbon-13 nuclear magnetic resonance (¹³C-NMR), electron impact (EI) mass spectra, and Fourier-transform infrared spectroscopy (FTIR). We synthesized two salts of disubstituted benzene triphenylphosphonium chloride (W1, W2) and characterized them by ¹H-NMR and FTIR. We synthesized two polymers by Wittig polycondensation from the reaction of F1 with salts (W1, W2) and characterized by ¹H-NMR, FTIR spectroscopy and gel permeation chromatography (GPC). Their photoluminescence properties were studied which giving light emission with λ_PL max at 502 and 472 nm for A1 and A2, respectively. We synthesized three polymers (P1, P2, P3) from reacting F1 with ketone by aldol condensation using KOH to give insoluble polymers and characterized them by FTIR spectroscopy. All polymers were evaluated by thermal gravimetric analysis (TGA), showing thermal stability with decomposition temperature beginning from 192 °C.

Keywords

conjugated polymers; fluorescent polymers; furan; Wittig polycondensation; aldol condensation

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DOI: https://doi.org/10.22146/ijc.104800