摘要
合成了两种非对称芳基取代的并三噻吩化合物.以2-溴-5-三甲基硅-二噻吩并[2,3-b:3′,2′-d]噻吩为原料,经脱除四甲基硅烷(TMS)和Suzuki偶联两步反应制备了2-噻吩基二噻吩并[2,3-b:3′,2′-d]噻吩,总产率为67.4%;以2-苯基二噻吩并[2,3-b:3′,2′-d]噻吩为原料,经N-溴代琥珀酰亚胺(简称NBS)溴代和Suzuki偶联两步反应制备了2-苯-5-噻吩基二噻吩并[2,3-b:3′,2′-d]噻吩,总产率为27.8%.产物经核磁共振谱(1H NMR,13C NMR)和质谱(MS)分析确认;利用紫外-可见分光光度法(UV-Vis)分析了合成产物的荧光特性.结果表明,由于苯基的存在,2-噻吩-5-苯基二噻吩并[2,3-b:3′,2′-d]噻吩分子的共轭体系增大,导致其吸收峰红移、发光能力减弱.
Two asymmetric aryl dithieno[2,3-b:3′,2′-d]thiophenes were synthesized.Namely,2-(thiophen-3-yl)dithieno[2,3-b:3′,2′-d]thiophene was synthesized in a total yield of 67.4% with 2-bromo-5-trimethylsilanyl-dithieno[2,3-b:3′,2′-d]-thiophene as the starting material,via removal of tetramethylsilane(TMS) group and Suzuki reaction.Then another asymmetric aryl dithieno[2,3-b:3′,2′-d]thiophene,2-phenyl-5-(thiophen-3-yl)dithieno[2,3-b:3′,2′-d]thiophene was synthesized in a total yield of 27.8% with 2-phenyldithieno[2,3-b:3′,2′-d]thiophene as raw material,via bromination by N-bromosuccinimide(NBS) combined with Suzuki reaction.Two title compounds were characterized by means of magnetic resonance spectroscopy and mass spectrometry.Their fluorescent characteristics were evaluated by means of ultraviolet-visible light(UV-Vis) spectrophotometry.Results indicate that 2-phenyl-5-(thiophen-3-yl)dithieno-[2,3-b:3′,2′-d]thiophene bearing phenyl group has a stronger conjugation system,showing red-shifted absorption spectra and decreased fluorescent intensity.
出处
《化学研究》
CAS
2011年第1期22-25,共4页
Chemical Research
基金
国家自然科学基金资助项目(20672028
50701016
50803015)
教育部基金资助项目(NCET-05-0610)
关键词
芳基并三噻吩
合成
光谱特性
aryl dithieno[2
3-b:3′
2′-d]thiophene
synthesis
spectroscopic properties