Strong binding affinity of a zinc-porphyrin-based receptor for halides through the cooperative effects of quadruple C-H hydrogen bonds and axial ligation

Chi Hwa Lee, Sangeun Lee, Hongsik Yoon, Woo Dong Jang

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

A new type of host compound (1), tetraphenyl zinc-porphyrin (ZnTPP) that contains four triazole groups at the ortho-position of each phenyl group, has been synthesized and characterized by using 1H, 13C NMR, and MALDI-TOF-MS analyses. The host-guest complex formation between 1 and halides was investigated by using 1H NMR spectroscopy in [D 6]DMSO. The triazole, benzyl, and phenylene proton signals were shifted upfield by the addition of halides in the form of tetrabutylammonium salts, which implies that the triazole protons in 1 are allocated very closely to the porphyrin ring and are directed toward the binding pocket over the porphyrin ring during the formation of hydrogen bonds. The UV/Vis absorption spectra showed that both the Soret and Q band absorptions of 1 underwent a strong redshift due to the addition of halides. Compound 1 exhibited surprisingly strong binding affinities for the halides, where the association constants for Cl-, Br-, and I- binding were estimated to be larger than 108, 1.79× 107, and 1.84× 105M-1, respectively. The UV/Vis absorption changes and the result of competitive titration using 4-tert-butylpyridine indicated that the cooperative effects of axial coordination and C-H⋯X hydrogen bond interactions resulted in the strong binding affinity of 1 to halides.

Original languageEnglish
Pages (from-to)13898-13903
Number of pages6
JournalChemistry - A European Journal
Volume17
Issue number49
DOIs
Publication statusPublished - 2011 Dec 2

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Triazoles
Porphyrins
Hydrogen bonds
Zinc
Protons
Absorption spectra
Dimethyl Sulfoxide
Titration
Nuclear magnetic resonance spectroscopy
Salts
Nuclear magnetic resonance
Association reactions
zinc hematoporphyrin

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Organic Chemistry

Cite this

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title = "Strong binding affinity of a zinc-porphyrin-based receptor for halides through the cooperative effects of quadruple C-H hydrogen bonds and axial ligation",
abstract = "A new type of host compound (1), tetraphenyl zinc-porphyrin (ZnTPP) that contains four triazole groups at the ortho-position of each phenyl group, has been synthesized and characterized by using 1H, 13C NMR, and MALDI-TOF-MS analyses. The host-guest complex formation between 1 and halides was investigated by using 1H NMR spectroscopy in [D 6]DMSO. The triazole, benzyl, and phenylene proton signals were shifted upfield by the addition of halides in the form of tetrabutylammonium salts, which implies that the triazole protons in 1 are allocated very closely to the porphyrin ring and are directed toward the binding pocket over the porphyrin ring during the formation of hydrogen bonds. The UV/Vis absorption spectra showed that both the Soret and Q band absorptions of 1 underwent a strong redshift due to the addition of halides. Compound 1 exhibited surprisingly strong binding affinities for the halides, where the association constants for Cl-, Br-, and I- binding were estimated to be larger than 108, 1.79× 107, and 1.84× 105M-1, respectively. The UV/Vis absorption changes and the result of competitive titration using 4-tert-butylpyridine indicated that the cooperative effects of axial coordination and C-H⋯X hydrogen bond interactions resulted in the strong binding affinity of 1 to halides.",
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Strong binding affinity of a zinc-porphyrin-based receptor for halides through the cooperative effects of quadruple C-H hydrogen bonds and axial ligation. / Lee, Chi Hwa; Lee, Sangeun; Yoon, Hongsik; Jang, Woo Dong.

In: Chemistry - A European Journal, Vol. 17, No. 49, 02.12.2011, p. 13898-13903.

Research output: Contribution to journalArticle

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