Detailed Information on Publication Record
2015
Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags
HORVÁTH, Peter, Peter ŠEBEJ, Tomáš ŠOLOMEK and Petr KLÁNBasic information
Original name
Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags
Authors
HORVÁTH, Peter (703 Slovakia, belonging to the institution), Peter ŠEBEJ (703 Slovakia, belonging to the institution), Tomáš ŠOLOMEK (703 Slovakia, belonging to the institution) and Petr KLÁN (203 Czech Republic, guarantor, belonging to the institution)
Edition
The journal of organic chemistry, 2015, 0022-3263
Other information
Language
English
Type of outcome
Článek v odborném periodiku
Field of Study
10401 Organic chemistry
Country of publisher
United States of America
Confidentiality degree
není předmětem státního či obchodního tajemství
References:
Impact factor
Impact factor: 4.785
RIV identification code
RIV/00216224:14310/15:00081568
Organization unit
Faculty of Science
UT WoS
000349934600002
Keywords in English
photochemistry; spectroscopy; pyronins; DFT calculations
Změněno: 11/2/2016 14:37, prof. RNDr. Petr Klán, Ph.D.
Abstract
V originále
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.
Links
GA13-25775S, research and development project |
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LM2011028, research and development project |
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LO1214, research and development project |
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