1. The Quest of Excited-State Intramolecular Proton Transfer via Eight-Membered Ring π-Conjugated Hydrogen Bonding System.
- Author
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Meng, Fan‐Yi, Hsu, Yen‐Hao, Zhang, Zhiyun, Wu, Pei‐Jhen, Chen, Yi‐Ting, Chen, Yi‐An, Chen, Chi‐Lin, Chao, Chi‐Min, Liu, Kuan‐Miao, and Chou, Pi‐Tai
- Subjects
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PROTON transfer reactions , *HYDROGEN bonding , *FLUORESCENCE , *CHEMICAL reactions , *PYRIDINE - Abstract
Searching for eight-membered ring π-conjugated hydrogen bonding (8-MR H-bonding) systems with excited-state intramolecular proton transfer (ESIPT) property is seminal and synthetically challenging. In this work, a series of π-conjugated molecules ( 8-HB-1, 8-HB-L1 and 8-HB-2) potentially possessing 8-MR H-bonding are strategically designed, synthesized and characterized. The configurations of these three potential molecules are checked by their X-ray structures, among which 8-HB-L1 (a structurally locked 8-HB-1 core chromophore) is proved to be an 8-MR H-bonding system, whereas 8-HB-1 and 8-HB-2 are too sterically hindered to form the 8-MR intramolecular H-bond. The ESIPT property of 8-HB-L1 is confirmed by the dual fluorescence consisting of normal and proton-transfer tautomer emissions. The insight into the ESIPT process of 8-HB-L1 is provided by femtosecond fluorescence upconversion measurements together with computational simulation. The results demonstrate for the first time a successful synthetic route to attain the 8-MR H-bonding molecule 8-HB-L1 with ESIPT property. [ABSTRACT FROM AUTHOR]
- Published
- 2017
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