近红外荧光探针增强共轭DDAO衍生物荧光团的理论设计及结构、电子和光谱性质研究  

Theoretical Design and Investigation of Structural,Electronic,and Spectral Properties of Enhanced Conjugated DDAO Derivative Fluorophores of Near-infrared Fluorescent Probes

作　　者：赵兵 胡泉源 张跃兴 ZHAO Bing;HU Quanyuan;ZHANG Yuexing(College of Chemistry and Chemical Engineering,Hubei University,Wuhan 430000,China;College of Chemistry and Chemical Engineering,Dezhou University,Dezhou 253023,China)

机构地区：[1]湖北大学化学化工学院,武汉430000 [2]德州学院化学化工学院,山东德州253023

出　　处：《湖北民族大学学报（自然科学版）》2024年第1期39-44,58,共7页Journal of Hubei Minzu University:Natural Science Edition

基　　金：有机功能分子合成与应用教育部重点实验室主任基金项目(KLSAOFM2007)。

摘　　要：为提升1,3-二氯-7-羟基-9,9-二甲基-2(9H)-吖啶酮(1,3-dichloro-7-hydroxy-9,9-dimethly-2(9H)-acridinone,DDAO)的荧光成像效果,从理论上设计了5种增强共轭DDAO衍生物,引入双氰基异佛尔酮,增强受体能力及DDAO衍生物的共轭程度。采用密度泛函理论(density functional theory,DFT)探讨了强共轭DDAO衍生物的荧光响应机制和特性,并分析DDAO及其衍生物优化后的结构变化、激发和发射过程中的电子转移及跃迁性质等。结果表明,DDAO衍生物的供体-π-受体(donor-π-acceptor,D-π-A)结构存在增强的分子内电荷转移(intramolecular charge transfer,ICT)效应,导致荧光发射波长最大移至1295.01 nm。该研究证实了引入取代基能产生强共轭,使激发前后产生较大的斯托克斯(Stokes)位移。In order to improve the fluorescence imaging effectiveness of 1,3-dichloro-7-hydroxy-9,9-dimethly-2(9H)-acridinone(DDAO),five enhanced conjugated DDAO derivatives were theoretically designed,and dicyanoisophorone was introduced as the enhanced receptor ability and the conjugation degree of the DDAO derivative.Density functional theory(DFT)was used to explore the fluorescence response mechanism and characteristics of strongly conjugated DDAO derivatives,and the optimized structural changes,electron transfer and transition properties of DDAO and its derivatives during excitation and emission were analyzed.The results show that there is an enhanced intramolecular charge transfer(ICT)effect in the donor-π-acceptor(D-π-A)structure of DDAO derivatives,resulting in a maximum fluorescence emission wavelength shift to 1295.01 nm.The final results confirm that the introduction of substituents produces strong conjugation,resulting in large Stokes shifts before and after excitation.

关 键 词：双氰基异佛尔酮 共轭程度 DDAO衍生物 密度泛函理论 π电子离域 ICT 

分 类 号：O643.31[理学—物理化学]