Zhang Zhengyi, Fang Hua
Department of Chemistry and Material Science, College of Science, Nanjing Forestry University, Nanjing, 210037, People's Republic of China.
J Fluoresc. 2024 Aug 21. doi: 10.1007/s10895-024-03914-3.
Recently, a new fluorescent senor based on 3-hydroxy-2-(naphthalen-2-yl)-4 H-chromen-4-one (HFN) for selective detection of HS was obtained in the experiment (Spectrochim. Acta Part A 271(2022)120962). Based on HFN, three new compounds (HFN1, HFN2 and HFN3) are designed to explore the influences of dimethylamine (-N(CH)) and cyano (-CN) groups on the excited-state intramolecular proton transfer (ESIPT) process and luminescent features of HFN. After analyzing the mainly geometrical parameters, electron densities and infrared spectra, we discovered that the intramolecular hydrogen bonds (IHBs) in the target molecules become stronger upon photo-excitation. Introducing -CN or/and -N(CH) groups into HFN indeed influences its ESIPT behavior and luminescent properties. The -N(CH) group enhances IHB, reduces ESIPT barrier and caused absorption/ fluorescence (at T form) peak blue-shift, while the -CN group shows a counterproductive effect. The coincidence of -N(CH) and -CN made the absorption/fluorescent wavelength of HFN red-shift more than single -N(CH) or -CN group does.
最近，在实验中获得了一种基于3-羟基-2-(萘-2-基)-4H-色烯-4-酮（HFN）的新型荧光传感器，用于选择性检测HS（《光谱化学学报》A辑271(2022)120962）。基于HFN，设计了三种新化合物（HFN1、HFN2和HFN3），以探究二甲胺（-N(CH)）和氰基（-CN）基团对HFN的激发态分子内质子转移（ESIPT）过程和发光特性的影响。在分析了主要几何参数、电子密度和红外光谱后，我们发现目标分子中的分子内氢键（IHB）在光激发时会变强。将-CN或/和-N(CH)基团引入HFN确实会影响其ESIPT行为和发光性质。-N(CH)基团增强了IHB，降低了ESIPT势垒，并导致吸收/荧光（T形式）峰蓝移，而-CN基团则表现出相反的效果。-N(CH)和-CN的共同作用使HFN的吸收/荧光波长红移程度比单个-N(CH)或-CN基团更大。
