Fluorescent properties of hydrogen-bonded ellipticine: A special effect of fluoride anion

Research output: Contribution to journalArticle

8 Citations (Scopus)

Abstract

Fluorescence properties of ellipticine, a plant alkaloid, was studied in the presence of hydrogen-bond acceptors, such as F-, CH3COO-, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and N-methylimidazole in different solvents. Global analysis of the spectrophotometric titration data proved that ellipticine deprotonation in the ground state occurred only in the case of the interaction with two F- anions in acetonitrile. The fluorescence band of the 1:1 complex of anions showed large Stokes shift implying significant proton displacement upon excitation along the hydrogen-bond. The lack of ellipticine-DBU complex emission was rationalized by quick proton transfer in the excited state. The kinetics and mechanism of the excited ellipticine quenching were also revealed.

Original languageEnglish
Pages (from-to)82-87
Number of pages6
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume182
Issue number1
DOIs
Publication statusPublished - Aug 20 2006

Fingerprint

ellipticine
Special effects
Fluorides
Anions
fluorides
Hydrogen
Hydrogen bonds
Negative ions
Fluorescence
hydrogen bonds
anions
Alkaloids
fluorescence
Deprotonation
alkaloids
Proton transfer
protons
hydrogen
Acetonitrile
Titration

Keywords

  • Ellipticine
  • Fluorescence
  • Hydrogen bonding
  • Proton transfer
  • Quenching

ASJC Scopus subject areas

  • Bioengineering
  • Physical and Theoretical Chemistry

Cite this

@article{bea4f2bd1e8a4d649448f0f2554e7096,
title = "Fluorescent properties of hydrogen-bonded ellipticine: A special effect of fluoride anion",
abstract = "Fluorescence properties of ellipticine, a plant alkaloid, was studied in the presence of hydrogen-bond acceptors, such as F-, CH3COO-, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and N-methylimidazole in different solvents. Global analysis of the spectrophotometric titration data proved that ellipticine deprotonation in the ground state occurred only in the case of the interaction with two F- anions in acetonitrile. The fluorescence band of the 1:1 complex of anions showed large Stokes shift implying significant proton displacement upon excitation along the hydrogen-bond. The lack of ellipticine-DBU complex emission was rationalized by quick proton transfer in the excited state. The kinetics and mechanism of the excited ellipticine quenching were also revealed.",
keywords = "Ellipticine, Fluorescence, Hydrogen bonding, Proton transfer, Quenching",
author = "Z. Miskolczy and L. Bicz{\'o}k",
year = "2006",
month = "8",
day = "20",
doi = "10.1016/j.jphotochem.2006.01.023",
language = "English",
volume = "182",
pages = "82--87",
journal = "Journal of Photochemistry and Photobiology A: Chemistry",
issn = "1010-6030",
publisher = "Elsevier",
number = "1",

}

TY - JOUR

T1 - Fluorescent properties of hydrogen-bonded ellipticine

T2 - A special effect of fluoride anion

AU - Miskolczy, Z.

AU - Biczók, L.

PY - 2006/8/20

Y1 - 2006/8/20

N2 - Fluorescence properties of ellipticine, a plant alkaloid, was studied in the presence of hydrogen-bond acceptors, such as F-, CH3COO-, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and N-methylimidazole in different solvents. Global analysis of the spectrophotometric titration data proved that ellipticine deprotonation in the ground state occurred only in the case of the interaction with two F- anions in acetonitrile. The fluorescence band of the 1:1 complex of anions showed large Stokes shift implying significant proton displacement upon excitation along the hydrogen-bond. The lack of ellipticine-DBU complex emission was rationalized by quick proton transfer in the excited state. The kinetics and mechanism of the excited ellipticine quenching were also revealed.

AB - Fluorescence properties of ellipticine, a plant alkaloid, was studied in the presence of hydrogen-bond acceptors, such as F-, CH3COO-, 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and N-methylimidazole in different solvents. Global analysis of the spectrophotometric titration data proved that ellipticine deprotonation in the ground state occurred only in the case of the interaction with two F- anions in acetonitrile. The fluorescence band of the 1:1 complex of anions showed large Stokes shift implying significant proton displacement upon excitation along the hydrogen-bond. The lack of ellipticine-DBU complex emission was rationalized by quick proton transfer in the excited state. The kinetics and mechanism of the excited ellipticine quenching were also revealed.

KW - Ellipticine

KW - Fluorescence

KW - Hydrogen bonding

KW - Proton transfer

KW - Quenching

UR - http://www.scopus.com/inward/record.url?scp=33746027010&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33746027010&partnerID=8YFLogxK

U2 - 10.1016/j.jphotochem.2006.01.023

DO - 10.1016/j.jphotochem.2006.01.023

M3 - Article

AN - SCOPUS:33746027010

VL - 182

SP - 82

EP - 87

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

SN - 1010-6030

IS - 1

ER -