Small-Molecule Fluorophores with Large Stokes Shifts:
9-Iminopyronin Analogues as Clickable Tags

J 2015

Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags

HORVÁTH, Peter; Peter ŠEBEJ; Tomáš ŠOLOMEK a Petr KLÁN

Základní údaje

Originální název

Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags

Autoři

HORVÁTH, Peter (703 Slovensko, domácí); Peter ŠEBEJ (703 Slovensko, domácí); Tomáš ŠOLOMEK (703 Slovensko, domácí) a Petr KLÁN (203 Česká republika, garant, domácí)

Vydání

The journal of organic chemistry, 2015, 0022-3263

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Spojené státy

Utajení

není předmětem státního či obchodního tajemství

Odkazy

URL

Impakt faktor

Impact factor: 4.785

Kód RIV

RIV/00216224:14310/15:00081568

Organizační jednotka

Přírodovědecká fakulta

DOI

http://dx.doi.org/10.1021/jo502213t

UT WoS

000349934600002

EID Scopus

2-s2.0-84922731746

Klíčová slova anglicky

photochemistry; spectroscopy; pyronins; DFT calculations

Štítky

AKR, rivok

Změněno: 11. 2. 2016 14:37, prof. RNDr. Petr Klán, Ph.D.

Anotace

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.

Návaznosti

GA13-25775S, projekt VaV

Název: Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

Investor: Grantová agentura ČR, Vývoj viditelným světlem aktivovatelných skupin a fluorescenčních značek pro chemii a biologii

LM2011028, projekt VaV

Název: RECETOX ? Národní infrastruktura pro výzkum toxických látek v prostředí

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, RECETOX Národní infrastruktura pro výzkum toxických látek v prostředí

LO1214, projekt VaV

Název: Centrum pro výzkum toxických látek v prostředí (Akronym: RECETOX)

Investor: Ministerstvo školství, mládeže a tělovýchovy ČR, Centrum pro výzkum toxických látek v prostředí

Citovat

HORVÁTH, Peter; Peter ŠEBEJ; Tomáš ŠOLOMEK a Petr KLÁN. Small-Molecule Fluorophores with Large Stokes Shifts: 9-Iminopyronin Analogues as Clickable Tags. The journal of organic chemistry. 2015, roč. 80, č. 3, s. 1299-1311. ISSN 0022-3263. Dostupné z: https://dx.doi.org/10.1021/jo502213t.

@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}. 2015, roč.~80, č.~3, s.~1299-1311. ISSN~0022-3263. Dostupné z: https://dx.doi.org/10.1021/jo502213t.

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