Synthesis of Excited-State Intramolecular Proton Transfer Compounds via Seven-Membered-Ring Hydrogen Bonding System
Date Issued
2014
Date
2014
Author(s)
Hsu, Yen-Hao
Abstract
In part I, we successfully obtained the bifunctional ortho- green fluorescence protein (o-HBDI) derivative, o-PyMeGFP, synthesized by Knoevenagel type reaction. Due to unstable conformation of o-MePyGFP; However, we successfully synthesized o-PyPhGFP via molecular adjustment. o-PyPhGFP underwent excited-state intramolecular proton transfer process via seven-membered-ring hydrogen-bonding system and its emssion at 607 nm. Also, ZnCl2 was reacted with o-PyPhGFP to form a complex, which destructed intramolecular H-bond and obtained blue emission.
In part II, according synthetic route from chapter1, 5-HI and 7-HI were used as starting reactants to obtain a structurally locked GFP core chromophore p-LHBDI, its ortho-derivative, o-LHBDI underwent ESIPT process and enhanced the quantum yield (up to 0.18) at 585 nm. We also synthesized H2BDI possessing both para- and ortho- hydroxyl groups. Anionic H2BDI rendered its emission at 557 nm and quantum yield of 1.3 x 10-3.
In part III, 1,2-dibromocyclopent-1-ene was used as starting reactant to link pyridine and pyrrole to obtain the novel compound, 7-HB, possessing intramolecular seven-membered-ring H-bond system. 7-HB rendered tautomer emission at 603 nm. Also, we obtained the methylated compound, 7-NCH3.
In part IV, three compounds (8-HB-1, 8-HB-2 and 8-HB-3) which were successfully synthesized may have intramolecular eight-membered-ring H-bond system.
Subjects
綠色螢光蛋白質
分子內氫鍵
Type
thesis
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