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@article{1335110,
author = {Horváth, Peter and Šebej, Peter and Šolomek, Tomáš and Klán, Petr},
article_number = {3},
doi = {http://dx.doi.org/10.1021/jo502213t},
keywords = {photochemistry; spectroscopy; pyronins; DFT calculations},
language = {eng},
issn = {0022-3263},
journal = {The journal of organic chemistry},
title = {Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags},
url = {http://pubs.acs.org/doi/abs/10.1021/jo502213t},
volume = {80},
year = {2015}
}
TY - JOUR
ID - 1335110
AU - Horváth, Peter - Šebej, Peter - Šolomek, Tomáš - Klán, Petr
PY - 2015
TI - Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags
JF - The journal of organic chemistry
VL - 80
IS - 3
SP - 1299-1311
EP - 1299-1311
SN - 00223263
KW - photochemistry
KW - spectroscopy
KW - pyronins
KW - DFT calculations
UR - http://pubs.acs.org/doi/abs/10.1021/jo502213t
N2 - The design, synthesis, and both experimental and theoretical studies of several novel 9-(acylimino)- and 9-(sulfonylimino)pyronin derivatives containing either an oxygen or a silicon atom at position 10 are reported. These compounds, especially the Si analogues, exhibit remarkably large Stokes shifts (around 200 nm) while still possessing a high fluorophore brightness, absorption bands in the near-UV and visible part of the spectrum, and high thermal and photochemical stabilities in protic solvents. The reason for the observed large Stokes shifts is an intramolecular charge-transfer excitation of an electron from the HOMO to the LUMO of the chromophore, accompanied by elongation of the C9-N bond and considerable solvent reorganization due to hydrogen bonding to the solvent. Due to the photophysical properties of the studied compounds and their facile and high-yielding synthesis, as well as a simple protocol for their bioorthogonal ligation to a model saccharide using a Huisgen alkyne-azide cycloaddition, they represent excellent candidates for biochemical and biological applications as fluorescent tags and indicators for multichannel imaging. 9-(Acylimino)pyronins alter their optical properties upon protonation and may also be used as pH sensors.
ER -
HORVÁTH, Peter, Peter ŠEBEJ, Tomáš ŠOLOMEK a Petr KLÁN. Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags. \textit{The journal of organic chemistry}. roč.~80, č.~3, s.~1299-1311. ISSN~0022-3263. doi:10.1021/jo502213t. 2015.
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