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Title: Locked ortho- and para-Core Chromophores of Green Fluorescent Protein;Dramatic Emission Enhancement via Structural Constraint
Authors: Yen-Hao Hsu;Yi-An Chen;Huan-Wei Tseng;Zhiyun Zhang;Jiun-Yi Shen;Wei-Ti Chuang;Tzu-Chieh Lin;Chun-Shu Lee;Wen-Yi Hung;Bor-Cherng Hong;Shih-Hung Liu;Pi-Tai Chou
Contributors: 國立臺灣海洋大學:光電科學研究所
Date: 2014
Issue Date: 2017-02-13T07:10:13Z
Publisher: Journal of American Chemical Society
Abstract: Abstract: We report the design strategy and synthesis of a structurally locked GFP core chromophore p-LHBDI, its ortho-derivative, o-LHBDI, and H2BDI possessing both para- and ortho-hydroxyl groups such that the inherent rotational motion of the titled compounds has been partially restricted. o-LHBDI possesses a doubly locked configuration, i.e., the seven-membered ring hydrogen bond and five-membered ring C(4-5-10-13-14) cyclization, from which the excited-state intramolecular proton transfer takes place, rendering a record high tautomer emission yield (0.18 in toluene) and the generation of amplified spontaneous emission. Compared with their unlocked counterparts, a substantial increase in the emission yield is also observed for p-LHBDI and H2BDI in anionic forms in water, and accordingly the structure versus luminescence relationship is fully discussed based on their chemistry and spectroscopy aspect. In solid, o-LHBDI exhibits an H-aggregate-like molecular packing, offers narrow-bandwidth emission, and has been successfully applied to fabricate a yellow organic light emitting diodes (λmax = 568 nm, ηext = 1.9%) with an emission full width at half-maximum as narrow as 70 nm.
Relation: 436(33)
Appears in Collections:[Institute of Optoelectronic Sciences] Periodical Articles

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