Tautocrowns: a concept for a sensing molecule with an active side-arm
Liudmil Antonov
1
,
Vanya Kurteva
1
,
S. Simeonov
1
,
Vera Deneva
1
,
Aurelien Crochet
2
,
Katharina Fromm
2
Publication type: Journal Article
Publication date: 2010-06-01
scimago Q3
wos Q2
SJR: 0.426
CiteScore: 4.1
Impact factor: 2.2
ISSN: 00404020, 14645416
Organic Chemistry
Drug Discovery
Biochemistry
Abstract
A new sensing molecule containing aza-15-crown-5 as a receptor and 4-(phenyldiazenyl)naphthalen-1-ol as a signal converter has been synthesized. In the free ligand, the hydrogen bonding between the tautomeric OH group and the nitrogen atom from the macrocycle fully shifts the tautomeric equilibrium towards the enol form. The complexation reverses the equilibrium as a result of the strong interaction between the metal ion captured in the macrocyclic moiety and the tautomeric carbonyl group. The complex formation is accompanied by strong bathochromic (between 60 and 100 nm) and hyperchromic effects on the absorption spectra. Obviously, the tautomeric OH/C O groups play the role of an active side-arm in the complexation, supporting it via formation of a 3D cavity and giving possibility for ejection of the guest compound under stimuli to shift the tautomeric process back.
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GOST
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Antonov L. et al. Tautocrowns: a concept for a sensing molecule with an active side-arm // Tetrahedron. 2010. Vol. 66. No. 24. pp. 4292-4297.
GOST all authors (up to 50)
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Antonov L., Kurteva V., Simeonov S., Deneva V., Crochet A., Fromm K. Tautocrowns: a concept for a sensing molecule with an active side-arm // Tetrahedron. 2010. Vol. 66. No. 24. pp. 4292-4297.
Cite this
RIS
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TY - JOUR
DO - 10.1016/j.tet.2010.04.049
UR - https://doi.org/10.1016/j.tet.2010.04.049
TI - Tautocrowns: a concept for a sensing molecule with an active side-arm
T2 - Tetrahedron
AU - Antonov, Liudmil
AU - Kurteva, Vanya
AU - Simeonov, S.
AU - Deneva, Vera
AU - Crochet, Aurelien
AU - Fromm, Katharina
PY - 2010
DA - 2010/06/01
PB - Elsevier
SP - 4292-4297
IS - 24
VL - 66
SN - 0040-4020
SN - 1464-5416
ER -
Cite this
BibTex (up to 50 authors)
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@article{2010_Antonov,
author = {Liudmil Antonov and Vanya Kurteva and S. Simeonov and Vera Deneva and Aurelien Crochet and Katharina Fromm},
title = {Tautocrowns: a concept for a sensing molecule with an active side-arm},
journal = {Tetrahedron},
year = {2010},
volume = {66},
publisher = {Elsevier},
month = {jun},
url = {https://doi.org/10.1016/j.tet.2010.04.049},
number = {24},
pages = {4292--4297},
doi = {10.1016/j.tet.2010.04.049}
}
Cite this
MLA
Copy
Antonov, Liudmil, et al. “Tautocrowns: a concept for a sensing molecule with an active side-arm.” Tetrahedron, vol. 66, no. 24, Jun. 2010, pp. 4292-4297. https://doi.org/10.1016/j.tet.2010.04.049.