Synthesis and Characterization of Polythiophenes Bearing Diphenyl Groups in the Conjugated Chain

来源 :Journal of Wuhan University of Technology(Materials Science | 被引量 : 0次 | 上传用户:hexiaole632
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4,4’-dibromo-2-nitro-biphenyl and 4,4’-dibromo-2,3’-dinitro-biphenyl have been synthesized via nitration reaction with 4,4′-dibromobiphenyl as the raw material. Three novel thiophene derivatives, 4, 4′-di(4-hexyl-thiophen-2-yl)biphenyl, 4,4′-di(4-hexyl-thiophen-2-yl)-2- nitro-biphenyl and 4,4′-di(4-hexyl-thiophen-2-yl)-2,3’-dinitrobiphenyl were synthesized through Stille coupling reaction, followed by polymerization in the presence of Fe Cl3, respectively. UV-vis absorption spectra, fluorescence spectra, photoluminescence spectra and electrochemical properties of the polymers were investigated. And the band-gap(Eg), HOMO orbital energy(EHOMO), and LUMO orbital energy(ELUMO) of the polymers were calculated. Among the polymers, polymer PBTN and PBTD show lower band-gap(2.67 and 2.63 e V), lower HOMO energy level(-5.38 and-5.4 e V) and broader wavelength(432 and 438 nm) than that of polymer PBTB(2.69 e V,-5.36 e V and 424 nm) with incorporation of one nitro group or two nitro groups in the main chain, respectively. 4,4’-dibromo-2-nitro-biphenyl and 4,4’-dibromo-2,3’-dinitro-biphenyl have been synthesized via nitration reaction with 4,4’-dibromobiphenyl as the raw material. Three novel thiophene derivatives , 4,4’-di (4-hexyl-thiophen-2-yl) biphenyl, 4,4’-di (4-hexyl-thiophen-2-yl) -2,3’-dinitrobiphenyl were synthesized through Stille coupling reaction, followed by polymerization in the presence of Fe Cl3, respectively. UV-vis absorption spectra, fluorescence spectra, photoluminescence spectra and electrochemical And the band-gap (Eg), HOMO orbital energy (EHOMO), and LUMO orbital energy (ELUMO) of the polymers were calculated. Among the polymers, polymer PBTN and PBTD show lower band-gap 2.67 and 2.63 eV), lower HOMO energy level (-5.38 and-5.4 eV) and broader wavelength (432 and 438 nm) than that of polymer PBTB (2.69 eV, -5.36 eV and 424 nm) with incorporation of one nitro group or two nitro grou ps in the main chain, respectively.
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