Synthesis of tautomerization-inhibited diamino substituted tetraphenylethene derivatives with different mechanochromisms: the vital role of chlorine

doi:10.1039/d0qm00940g

	Synthesis of tautomerization-inhibited diamino substituted tetraphenylethene derivatives with different mechanochromisms: the vital role of chlorine
	Li, Xin 1; Zhou, Linsen 2; Cheng, Zheng 1,3; Ran, Qichao 1; Wang, Xu 1; Zhuang, Yongbing 4; Luo, Longbo 1; Liu, Xiangyang 1
刊名	MATERIALS CHEMISTRY FRONTIERS
	2021-03-07
卷号	5 期号:5 页码:2387-2398
DOI	10.1039/d0qm00940g
英文摘要	The stereochemistry of tetraphenylethene (TPE) derivatives with aggregation induced emission (AIE) characteristics has demonstrated significant value in advanced materials and life sciences. Geometric Z/E-diamino substituted TPE (Z/E-2NH(2)-TPE) suffers from tautomerization and separation. To resolve this problem, pure geometric Z/E diamino and dichloro dual-substituted TPE (Z/E-2Cl-2NH(2)-TPE) molecules were designed precisely and separated via common column chromatography by introducing chlorine. Tautomerization would not occur even after being kept at increased temperature (200 degrees C) for 2 hours or at room temperature for 6 months. The role of chlorine atoms in geometric Z/E-2Cl-2NH(2)-TPE molecules has been deeply elucidated through theoretical computational chemistry methods and intermolecular interaction. Compared with Z/E-2NH(2)-TPE molecules, the Frank-Condon excitation, transition state of the tautomerization process, conical intersection, and photoluminescence in the potential energy surface of Z/E-2Cl-2NH(2)-TPE molecules were similar to those of Z/E-2NH(2)-TPE molecules. The energy barrier of tautomerization seldom clarified the role of the chlorine atoms while enhanced intermolecular interaction provided by chlorine atoms effectively rigidified the conformation of the tautomerization process. Thereafter, different mechanochromism (MC) photochemical properties were probed in depth, which were induced by structure-dependent molecules' H/J-aggregation state and reorganization energy. The tautomerization-inhibited Z/E-2Cl-2NH(2)-TPE molecules with a reactive functional group provided a good template for designing advanced materials.
资助项目	National Natural Science Foundation of China[51873113] ; National Natural Science Foundation of China[51633004] ; Program of Science and Technology of Sichuan Province[2018GZ0153] ; China Postdoctoral Science Foundation[2018M643472]
WOS关键词	AGGREGATION-INDUCED EMISSION
WOS研究方向	Chemistry ; Materials Science
语种	英语
出版者	ROYAL SOC CHEMISTRY
WOS记录号	WOS:000626507700023
资助机构	National Natural Science Foundation of China ; Program of Science and Technology of Sichuan Province ; China Postdoctoral Science Foundation
内容类型	期刊论文
源URL	[http://ir.ipe.ac.cn/handle/122111/48046]
专题	中国科学院过程工程研究所
通讯作者	Luo, Longbo; Liu, Xiangyang
作者单位	1.Sichuan Univ, Coll Polymer Sci & Engn, State Key Lab Polymer Mat & Engn, Chengdu 610065, Peoples R China 2.China Acad Engn Phys, Inst Mat, Jiangyou 621908, Peoples R China 3.Nankai Univ, Coll Mat Sci & Engn, Tianjin 300350, Peoples R China 4.Chinese Acad Sci, Univ Chinese Acad Sci, Inst Proc Engn, State Key Lab Biochem Engn, Beijing 100190, Peoples R China
推荐引用方式 GB/T 7714	Li, Xin,Zhou, Linsen,Cheng, Zheng,et al. Synthesis of tautomerization-inhibited diamino substituted tetraphenylethene derivatives with different mechanochromisms: the vital role of chlorine[J]. MATERIALS CHEMISTRY FRONTIERS,2021,5(5):2387-2398.
APA	Li, Xin.,Zhou, Linsen.,Cheng, Zheng.,Ran, Qichao.,Wang, Xu.,...&Liu, Xiangyang.(2021).Synthesis of tautomerization-inhibited diamino substituted tetraphenylethene derivatives with different mechanochromisms: the vital role of chlorine.MATERIALS CHEMISTRY FRONTIERS,5(5),2387-2398.
MLA	Li, Xin,et al."Synthesis of tautomerization-inhibited diamino substituted tetraphenylethene derivatives with different mechanochromisms: the vital role of chlorine".MATERIALS CHEMISTRY FRONTIERS 5.5(2021):2387-2398.