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Binding ability of first and second generation/carbazolylphenyl dendrimers with Zn(II) tetraphenylporphyrin core towards small heterocyclic substrates

Nguyen, Tran Nguyen; Mamardashvili, Galina M.; Kulikova, Olga M.; Scheblykin, Ivan LU ; Mamardashvili, Nugzar Zh. and Dehaen, Wim (2014) In RSC Advances 4(38). p.19703-19709
Abstract
A study of complex formation of Zn(II) tetraarylporphyrin dendrimers with carbazolylphenyl branches towards 1,4-diazabicyclo-[2.2.2]octane, pyridine, imidazole, N-methylimidazole and 1,2,3-triazole was carried out by spectrophotometric and H-1 NMR titration methods. It has been shown that the binding ability of the porphyrin receptors towards mono and bidentate N-containing substrates depends on the nature, number and generation of the branches. Bulky substituents are able either to significantly reduce the binding ability of the tetrapyrrolic cores due to the shielding of the porphyrin reaction centres, or to significantly increase it by forming intramolecular cavities for complementary binding of substrates. It has been determined that... (More)
A study of complex formation of Zn(II) tetraarylporphyrin dendrimers with carbazolylphenyl branches towards 1,4-diazabicyclo-[2.2.2]octane, pyridine, imidazole, N-methylimidazole and 1,2,3-triazole was carried out by spectrophotometric and H-1 NMR titration methods. It has been shown that the binding ability of the porphyrin receptors towards mono and bidentate N-containing substrates depends on the nature, number and generation of the branches. Bulky substituents are able either to significantly reduce the binding ability of the tetrapyrrolic cores due to the shielding of the porphyrin reaction centres, or to significantly increase it by forming intramolecular cavities for complementary binding of substrates. It has been determined that due to a good geometric match of the ligand's size with the size of the intramolecular cavities of the porphyrin receptors, and by the existence of additional hydrogen bonding and/or pi-pi interactions between the ligand and the triazole fragments of the porphyrin the Zn-tetraarylporphyrins with eight 4-carbazolylphenyl-1,2,3-triazole end groups of the first and the second generations could be used as effective receptors for imidazole, N-methylimidazole and 1,2,3-triazole. Taking into account the fact that binding is accompanied by a clear and easily identifiable response in the UV-Vis spectra of the reaction mixture, these metalloporphyrins could be considered as molecular optical sensing devices for small heterocyclic substrates. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
RSC Advances
volume
4
issue
38
pages
19703 - 19709
publisher
Royal Society of Chemistry
external identifiers
  • wos:000335922900021
  • scopus:84899888920
ISSN
2046-2069
DOI
10.1039/c3ra45660a
language
English
LU publication?
yes
id
64ac93c1-cbbc-4634-8cf5-895344f8e9ce (old id 4482268)
date added to LUP
2014-06-19 13:38:19
date last changed
2017-08-27 04:49:48
@article{64ac93c1-cbbc-4634-8cf5-895344f8e9ce,
  abstract     = {A study of complex formation of Zn(II) tetraarylporphyrin dendrimers with carbazolylphenyl branches towards 1,4-diazabicyclo-[2.2.2]octane, pyridine, imidazole, N-methylimidazole and 1,2,3-triazole was carried out by spectrophotometric and H-1 NMR titration methods. It has been shown that the binding ability of the porphyrin receptors towards mono and bidentate N-containing substrates depends on the nature, number and generation of the branches. Bulky substituents are able either to significantly reduce the binding ability of the tetrapyrrolic cores due to the shielding of the porphyrin reaction centres, or to significantly increase it by forming intramolecular cavities for complementary binding of substrates. It has been determined that due to a good geometric match of the ligand's size with the size of the intramolecular cavities of the porphyrin receptors, and by the existence of additional hydrogen bonding and/or pi-pi interactions between the ligand and the triazole fragments of the porphyrin the Zn-tetraarylporphyrins with eight 4-carbazolylphenyl-1,2,3-triazole end groups of the first and the second generations could be used as effective receptors for imidazole, N-methylimidazole and 1,2,3-triazole. Taking into account the fact that binding is accompanied by a clear and easily identifiable response in the UV-Vis spectra of the reaction mixture, these metalloporphyrins could be considered as molecular optical sensing devices for small heterocyclic substrates.},
  author       = {Nguyen, Tran Nguyen and Mamardashvili, Galina M. and Kulikova, Olga M. and Scheblykin, Ivan and Mamardashvili, Nugzar Zh. and Dehaen, Wim},
  issn         = {2046-2069},
  language     = {eng},
  number       = {38},
  pages        = {19703--19709},
  publisher    = {Royal Society of Chemistry},
  series       = {RSC Advances},
  title        = {Binding ability of first and second generation/carbazolylphenyl dendrimers with Zn(II) tetraphenylporphyrin core towards small heterocyclic substrates},
  url          = {http://dx.doi.org/10.1039/c3ra45660a},
  volume       = {4},
  year         = {2014},
}