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

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。

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.