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Synthesis of tautomerization-inhibited diamino substituted tetraphenylethene derivatives with different mechanochromisms: the vital role of chlorine
Li, Xin1; Zhou, Linsen2; Cheng, Zheng1,3; Ran, Qichao1; Wang, Xu1; Zhuang, Yongbing4; Luo, Longbo1; Liu, Xiangyang1
2021-03-07
Source PublicationMATERIALS CHEMISTRY FRONTIERS
Volume5Issue:5Pages:2387-2398
AbstractThe 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.
DOI10.1039/d0qm00940g
Language英语
WOS KeywordAGGREGATION-INDUCED EMISSION
Funding ProjectNational 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 Research AreaChemistry ; Materials Science
WOS SubjectChemistry, Multidisciplinary ; Materials Science, Multidisciplinary
Funding OrganizationNational Natural Science Foundation of China ; Program of Science and Technology of Sichuan Province ; China Postdoctoral Science Foundation
WOS IDWOS:000626507700023
PublisherROYAL SOC CHEMISTRY
Citation statistics
Document Type期刊论文
Identifierhttp://ir.ipe.ac.cn/handle/122111/48047
Collection中国科学院过程工程研究所
Corresponding AuthorLuo, Longbo; Liu, Xiangyang
Affiliation1.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
Recommended Citation
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.
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