Multiple Hydrogen Bonds Promoted ESIPT and AlE-active Chiral Salic-ylaldehyde Hydrazide  

作　　者：Man Wang Caiqi Cheng Jintong Song Jun Wang Xiangge Zhou Haifeng Xiang Jin Liu 

机构地区：[1]College of Chemistry, Sichuan University, Chengdu, Sichuan 610041, China [2]State Key Laboratory of Oral Diseases, Department of Orthodontics, West China Hospital of Stomatology, Sichuan University, Chendu, Sichuan 610064, China [3]Laboratory of Stem Cell Biology, West China Hospital, Sichuan University, Chengdu, Sichuan 610064, China

出　　处：《Chinese Journal of Chemistry》2018年第8期698-707,共10页中国化学（英文版）

基　　金：This work was supported by the National Natural Science Foundation of China （No. 21372169） and Sichuan Provincial Foundation （2008SG0021）. We acknowledge the comprehensive training platform of the specialized laboratory of the College of Chemistry, Sichuan University, for material analysis. We acknowledge the comprehensive training platform of the specialized laboratory of the College of Chemistry, Sichuan University, for material analysis. We would like to thank the Analytical ＆ Testing Center of Sichuan University for CCD X-ray single crystal diffractometer work and circular dichroism CD spectrometer work. We are grateful to Daibing Luo and Yani Xie for help with the single crystal and circular dichroism measurements.

摘　　要：The simpler, the better! A series of simple and highly fluorescent salicylaldehyde hydrazide molecules （41 samples） have been designed and prepared. Even though these soft materials contain a very small π-conjugated system, they can go through multiple intramolecular and intermolecular hydrogen bonds promoted excited-state intramolecular proton-transfer （ESIPT） to display strong blue, green, yellow, and orange aggregation-induced emission （ALE） with large Stokes shifts （up to 184 nm） and high fluorescence quantum yields （φ up to 0.20）. Unusual mechanochromic fluorescence en- hancements are also found in some solid samples. Through coordination, hydrogen and halogen bonds, these flexible molecules can be used as Mg2＋ （φ up to 0.46） probes, universal anion （φ up to 0.14） and unprotected amino acids （φ up to 0.16） probes, and chiral diamine （enantiomeric selectivity and φ up to 0.36 and 0.062, respectively） receptors. Combining their advantages of AlE and biocompatibility, these low cytotoxic dyes have potential application in living cell imaging. Furthermore, the effects of different functional groups on the molecule arrangement, ESIPT, AlE, probe, and chiral recognition properties are also examined, which provide a simple and bright paradigm for the design of multiple-stimuli-responsive smart materials.The simpler, the better! A series of simple and highly fluorescent salicylaldehyde hydrazide molecules （41 samples） have been designed and prepared. Even though these soft materials contain a very small π-conjugated system, they can go through multiple intramolecular and intermolecular hydrogen bonds promoted excited-state intramolecular proton-transfer （ESIPT） to display strong blue, green, yellow, and orange aggregation-induced emission （ALE） with large Stokes shifts （up to 184 nm） and high fluorescence quantum yields （φ up to 0.20）. Unusual mechanochromic fluorescence en- hancements are also found in some solid samples. Through coordination, hydrogen and halogen bonds, these flexible molecules can be used as Mg2＋ （φ up to 0.46） probes, universal anion （φ up to 0.14） and unprotected amino acids （φ up to 0.16） probes, and chiral diamine （enantiomeric selectivity and φ up to 0.36 and 0.062, respectively） receptors. Combining their advantages of AlE and biocompatibility, these low cytotoxic dyes have potential application in living cell imaging. Furthermore, the effects of different functional groups on the molecule arrangement, ESIPT, AlE, probe, and chiral recognition properties are also examined, which provide a simple and bright paradigm for the design of multiple-stimuli-responsive smart materials.

关 键 词：promoted excited-state intramolecular proton-transfer （ESIPT） aggregation-induced emission anion hosts/probes amino acids probes chiral diamine 

分 类 号：TS262.5[轻工技术与工程—发酵工程] S858.363[轻工技术与工程—食品科学与工程]