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Meng FY, Hsu YH, Zhang Z, et al. The Quest of Excited-State Intramolecular Proton Transfer via Eight-Membered Ring π-Conjugated Hydrogen Bonding System. Chem Asian J. 2017;12(23):3010-3015doi: 10.1002/asia.201701057.
Meng, F. Y., Hsu, Y. H., Zhang, Z., Wu, P. J., Chen, Y. T., Chen, Y. A., Chen, C. L., Chao, C. M., Liu, K. M., & Chou, P. T. (2017). The Quest of Excited-State Intramolecular Proton Transfer via Eight-Membered Ring π-Conjugated Hydrogen Bonding System. Chemistry, an Asian journal, 12(23), 3010-3015. https://doi.org/10.1002/asia.201701057
Meng, Fan-Yi, et al. "The Quest of Excited-State Intramolecular Proton Transfer via Eight-Membered Ring π-Conjugated Hydrogen Bonding System." Chemistry, an Asian journal vol. 12,23 (2017): 3010-3015. doi: https://doi.org/10.1002/asia.201701057
Meng FY, Hsu YH, Zhang Z, Wu PJ, Chen YT, Chen YA, Chen CL, Chao CM, Liu KM, Chou PT. The Quest of Excited-State Intramolecular Proton Transfer via Eight-Membered Ring π-Conjugated Hydrogen Bonding System. Chem Asian J. 2017 Dec 05;12(23):3010-3015. doi: 10.1002/asia.201701057. Epub 2017 Oct 30. PMID: 28980416.
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Chem Asian J. 2017 Dec 05;12(23):3010-3015. doi: 10.1002/asia.201701057. Epub 2017 Oct 30.

The Quest of Excited-State Intramolecular Proton Transfer via Eight-Membered Ring π-Conjugated Hydrogen Bonding System.

Chemistry, an Asian journal

Fan-Yi Meng, Yen-Hao Hsu, Zhiyun Zhang, Pei-Jhen Wu, Yi-Ting Chen, Yi-An Chen, Chi-Lin Chen, Chi-Min Chao, Kuan-Miao Liu, Pi-Tai Chou

Affiliations

  1. Department of Chemistry, National Taiwan University, Taipei, 10617, Taiwan, R.O.C.
  2. Department of Medical Applied Chemistry, Department of Medical Education, Chung Shan Medical University, Taichung, 40201, Taiwan, R.O.C.

PMID: 28980416 DOI: 10.1002/asia.201701057

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.

© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

Keywords: eight-membered rings; fluorescence; hydrogen bonds; proton transfer; single crystals

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