具有扭曲的分子内电荷转移的芳香酮衍生物的结构与光谱性能研究
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摘要
设计合成了一系列基于芳香酮的具有扭曲的分子内电荷转移(TICT)结构特性的化合物,通过线性光物理性质与双光子吸收性质的表征,研究了分子结构中不同共轭基团和不同取代基位置对化合物光谱性能的影响,同时通过溶剂效应研究了化合物的分子内电荷转移性质。结合理论计算结果表明分子的共轭骨架和取代基的位置都能显著影响分子内电荷转移特征。其中芴酮系列的化合物表现出了较强的双光子吸收与聚集诱导荧光增强效应,在生物荧光成像领域有着潜在的应用价值。
A series of compounds with twisted intramolecular charge transfer( TICT) based on aromatic ketone derivatives were synthesized and characterized. The effects of different conjugated groups and substituent positions on the spectral properties of these compounds were studied by characterization of their linear photophysical and two-photon absorption properties. Additionally,the intramolecular charge transfer properties of these compounds were also studied by solvent effect. Combined with theoretical calculations,the results showed that the molecular conjugated skeleton and the position of substituents can significantly affect the intramolecular charge transfer characteristics.Fluorenone based compounds exhibite strong two-photon absorption and aggregation-induced fluorescence enhancement effects,which have potential applications in biological imaging.
A series of compounds with twisted intramolecular charge transfer( TICT) based on aromatic ketone derivatives were synthesized and characterized. The effects of different conjugated groups and substituent positions on the spectral properties of these compounds were studied by characterization of their linear photophysical and two-photon absorption properties. Additionally,the intramolecular charge transfer properties of these compounds were also studied by solvent effect. Combined with theoretical calculations,the results showed that the molecular conjugated skeleton and the position of substituents can significantly affect the intramolecular charge transfer characteristics.Fluorenone based compounds exhibite strong two-photon absorption and aggregation-induced fluorescence enhancement effects,which have potential applications in biological imaging.
引文
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[2] A C Benniston,A Harriman. Chem. Soc. Rev.,2006,35(2):169~179.
[3] G Ramakrishna,T Goodson. J. Phys. Chem. A,2007,111(6):993~1000.
[4] G S He,L S Tan,Q Zheng et al. Chem. Rev.,2008,108(4):1245~1330.
[5] F Helmchen,W Denk. Nat. Methods,2005,2(12):932~940.
[6] K S Lee,R H Kim,D Y Yang et al. Prog. Polym. Sci.,2008,33(6):631~681.
[7] Z Sun,L P Zhang,F Wu et al. Adv. Funct. Mater.,2017,27(48):1704079.
[8] K Rurack:Fluorescence Quantum Yields:Methods of Determination and Standards, Standardization and Quality Assurance in Fluorescence Measurements I,2008:101~145.
[9] A L Capodilupo,V Vergaro,E Fabiano et al. J. Mater. Chem.B,2015,3(16):3315~3323.
[10] N S Makarov,M Drobizhev,A Rebane. Opt. Express,2008,16(6):4029~4047.
[11] D Cvejn,E Michail,K Seintis et al. RSC Adv.,2016,6(16):12819~12828.
[12] J R Lakowicz. Principles of Fluorescence Spectroscopy.Springer Science&Business Media,2013.
[13] M J Frisch,G W Trucks,H B Schlegel et al. Gaussian 09.Wallingford,CT,2009.