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湾位双键官能化苝酰亚胺的合成及其溶液自组装行为研究

Synthesis and solution self-assembly behavior study of bay-site double bond functionalized perylene diimide

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【作者】 赵浩儒鄂曾泽顾丹丹桑伟慧韩天娇廖作桂陈珈江晓泽孙宾

【Author】 Zhao Haoru;E Zengze;Gu Dandan;Sang Weihui;Han Tianjiao;Liao Zuogui;Chen Jia;Jiang Xiaoze;Sun Bin;State Key Laboratory for Modification of Chemical Fibers and Polymer Materials, College of Materials Science and Engineering, Donghua University;Guangdong Yinuo Composite Material Co., Ltd.;

【通讯作者】 陈珈;江晓泽;孙宾;

【机构】 东华大学材料科学与工程学院纤维材料改性国家重点实验室广东壹诺科技股份有限公司

【摘要】 通过对苝酰亚胺的改性,合成了湾位双键官能团化、侧链为燕尾链的苝酰亚胺衍生物1,7-vinyl-PDI-EH。通过控制变量、优化合成反应条件,以反应浓度3.5 mg/mL在色谱纯级别(HPLC)四氢呋喃中反应2 h时,目标产物产率最高。进一步采用紫外可见分光光谱、荧光光谱以及浓度依赖光谱对其光物理性能和自组装行为进行表征,结果表明1,7-vinyl-PDI-EH在氯仿溶液中浓度达到1.1×10-4 mol/L后随着浓度增大荧光淬灭,7.0×10-4 mol/L时分子产生明显自组装。通过氯仿和甲醇体系的双扩散晶体培养,得到1,7-vinyl-PDI-EH晶体,其在结晶状态下仍有一定荧光性能。

【Abstract】 A new perylene diimide derivative called 1,7-vinyl-PDI-EH was synthesized, containing a double bond at the bay site and a swallow-tailed side chain at the imide site. The reaction conditions were optimized, and the highest yield of 1,7-vinyl-PDI-EH was achieved at a concentration of 3.5 mg/ml in HPLC-grade tetrahydrofuran with a reaction time of 2 hours. The photophysical properties and solution self-assembly behavior were characterized using UV-Vis and fluorescence spectroscopy. As the concentration increased above 1.1×10-4 mol/L in chloroform solution, fluorescence quenching was observed, with the self-assembly concentration of 1,7-vinyl-PDI-EH determined to be 7.0×10-4 mol/L. Crystals of 1,7-vinyl-PDI-EH were obtained using a double-diffusion method in a chloroform/methanol system and exhibited fluorescence in the crystalline state.

  • 【文献出处】 合成技术及应用 ,Synthetic Technology & Application , 编辑部邮箱 ,2024年02期
  • 【分类号】O625.525;O641.3
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