Comparative Photophysical Study of Differently Substituted Cinnamaldehyde-Based Chalcones: From Intramolecular Charge Transfer to Fluorogenic Solvent Selectivity
作者:Arghyadeep Bhattacharyya、Subhash Chandra Makhal、Nikhil Guchhait
DOI:10.1021/acs.jpca.9b03437
日期:2019.8.1
We synthesized three cinnamaldehyde-based chalcone derivatives, (2E,4E)-1-(2-hydroxyphenyl)-5-phenylpenta-2,4-dien-1-one (HPD), (2E,4E)-5-(4-(dimethylamino)phenyl)-1-phenylpenta-2,4-dien-1-one (DPPD), and (2E,4E)-5-(4-(dimethylamino)phenyl)-1-(2-hydroxyphenyl)penta-2,4-dien-1-one (DPHPD). The molecule HPD was totally nonfluorescent. Exclusion of a phenolic −OH moiety from HPD along with the introduction
我们合成了三种基于肉桂醛的查尔酮衍生物,(2E,4E)-1-(2-羟苯基)-5-苯基戊-2,4-二烯-1-酮(HPD),(2E,4E)-5-(4 -(二甲氨基)苯基)-1-苯基戊-2,4-二烯-1-酮(DPPD)和(2E,4E)-5-(4-(二甲氨基)苯基)-1-(2-羟基苯基)戊-2,4-dien-1-one(DPHPD)。HPD分子是完全不发荧光的。从HPD中排除酚类-OH部分,并在DPPD中引入二甲基氨基部分会导致溶液相具有出色的激发态电荷转移性质。有趣的是,在DPHPD中引入酚类-OH和二甲基氨基部分会导致在激发态下的溶剂选择性。DPHDP仅在含羰基或硫代羰基的溶剂(例如二甲亚砜(DMSO),二甲基甲酰胺(DMF)和二甲基乙酰胺(DMAC))中表现为强荧光团,并在紫外光下显示突出的红色。但是,在类似的羰基化溶剂(如丙酮或甲酰胺)或粘性介质(如甘油)中未观察到发射。通过各种光谱技术探