Meta-CF3-Substituted Analogues of the GFP Chromophore with Remarkable Solvatochromism

Abstract

In this work, we have shown that the introduction of a trifluoromethyl group into the me-ta-position of arylidene imidazolones (GFP chromophore core) leads to a dramatic increase in their fluorescence in nonpolar and aprotic media. The presence of a pronounced solvent-dependent gradation of fluorescence intensity makes it possible to use these substances as fluorescent polarity sensors. In particular, we showed that one of the created compounds could be used for selective labeling of the endoplasmic reticulum of living cells.

Synthesis of Spiro[imidazole‐4,3′‐pyrrolo[1,2‐a]quinolin]‐ 5‐ones via 1,3‐Dipolar Cycloaddition of Quinolinium Ylides with Arylydeneimidazol‐4‐ones

“…The authors have cited additional references within the Supporting Information. [38][39][40][41][42]…”

“…The detailed experimental procedures and spectral data, copies of 1 H and 13 C NMR spectra are available in the Supporting Information. The authors have cited additional references within the Supporting Information [38–42] …”

meta-Fluorophores: an uncharted ocean of opportunities

“…Green fluorescent protein (GFP) and its chromophore (Chart 1) 13–34 opened a new domain for exploring the fluorophore structure towards imaging in a biological medium. Although GFP is highly fluorescent in an aqueous medium, the wild-type GFP chromophore (Chart 1) is nearly non-luminescent in an aqueous medium.…”

“…Based on several meta -GFP chromophore analogues the following electronic or optical spectroscopic conclusions have been drawn: 13–34…”