Synthesis and luminescence properties of analogues of the green fluorescent protein chromophore

authors	Esteves, CIC; Fonseca, ID; Rocha, J; Silva, AMS; Guieu, S
nationality	International
journal	DYES AND PIGMENTS
author keywords	Green fluorescent protein; Aggregation-induced emission enhancement; Synthesis; Fluorescence
keywords	GFP-CHROMOPHORE; EMISSION ENHANCEMENT; NITRO
abstract	The green fluorescent protein (GFP) is extensively used as a biomarker for fluorescence biological imaging. The chromophore in GFP is only fluorescent when confined into the beta-barrel of the protein. Similarly, synthetic analogues of the fluorophore of GFP are usually non-emissive in solution, due to free rotation around the aryl-alkene bond and (Z/E)-isomerization of the double bond. Here, the synthesis and characterization of three analogues of the fluorophore of GFP are reported. The introduction of more electron donating substituents induces a red-shift in the absorption and emission. The fluomphores are more emissive in the solid state than in solution, and a study of their crystal structure reveals that the (Z/E)-isomerization is efficiently blocked in the crystals.
publisher	ELSEVIER SCI LTD
issn	0143-7208
isbn	1873-3743
year published	2020
volume	177
digital object identifier (doi)	10.1016/j.dyepig.2020.108267
web of science category	Chemistry, Applied; Engineering, Chemical; Materials Science, Textiles
subject category	Chemistry; Engineering; Materials Science
unique article identifier	WOS:000525303800018