Appending zinc tetraphenylporphyrin with an amine receptor at β-pyrrolic carbon for designing a selective histamine chemosensor

Qian Ni Guo, Zao Ying Li, Wing Hong CHAN*, Kai Chung Lau, Maxwell J. Crossley

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

9 Citations (Scopus)

Abstract

Adopting the rarely used β-functionalisation strategy in porphyrin-based sensor design, an amine receptive site is appended onto the zinc(II) porphyrin molecular framework affording a ditopic chemosensor 4. The assembled chemosensor interacts selectively with histamine in toluene via a 'two-site' binding mode. Association constant of the complex evaluated from the respective UV-vis spectra is found to be (2.32 ± 0.57) × 106, which is approximately 4-fold greater than those complexes derived from 4 and nicotine/histidine. On the basis of a combined spectroscopic method and molecular modelling, the binding model of the porphyrin host and biogenic guest molecules is established. Our results clearly demonstrate the viability of the design and development of the porphyrin-based chemosensor by appending a receptor at the β-pyrrolic carbon of the porphyrin scaffold.

Original languageEnglish
Pages (from-to)122-129
Number of pages8
JournalSupramolecular Chemistry
Volume22
Issue number2
DOIs
Publication statusPublished - Feb 2010

Scopus Subject Areas

  • Chemistry(all)

User-Defined Keywords

  • Ditopic chemosensor
  • Histamine sensing
  • Zinc tetraphenylporphyrin
  • β-functionalisation

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