Chromogenic indicator for anion reporting based on an N-substituted oxoporphyrinogen

Hill, Jonathan P.; Schumacher, Amy Lea; D'Souza, Francis; Labuta, Jan; Redshaw, Carl; Elsegood, Mark R.J.; Aoyagi, Masaru; Nakanishi, Takashi; Ariga, Katsuhiko

Abstract

5,10,15,20-Tetrakis-3,5-di-tert-butyl-4-oxocyclohexadienylidene porphyrinogen and its di-N-benzylated derivative are solvatochromic dyes capable of binding anionic species. The influence of solvent polarity and hydrogen bonding on their electronic absorption spectra was observed. Hydrogen bonding by the porphyrinogen amine protons of acetone solvent molecules could be observed in the solid state. The acetone solvate of N21N23- dibenzyl-5,10,15,20-tetrakis-3,5-di-fer?-butyl-4-oxocyclohexadienylidene porphyrinogen crystallized under anhydrous conditions in the space group P1 with cell dimensions a = 12.1693(11) Å, b = 17.5849(13) Å, c = 21.0965(17) Å, α = 69.870(4)°, β = 78.140(4)°, γ = 82.865(5)°. These porphyrinogens are capable of binding a variety of anions and can be used to distinguish fluoride chromogenically from the other halide anions. Solvatochromism was combined with anion binding in an attempt to provide more selective tests for anions. The anion binding properties were investigated using UV/vis spectrophotometry and 1H NMR spectroscopy. © 2006 American Chemical Society.

Citation

Hill, J. P., Schumacher, A. L., D'Souza, F., Labuta, J., Redshaw, C., Elsegood, M. R., Aoyagi, M., Nakanishi, T., & Ariga, K. (2006). Chromogenic indicator for anion reporting based on an N-substituted oxoporphyrinogen. Inorganic chemistry, 45(20), 8288-8296. https://doi.org/10.1021/ic0611591

• Journal Article Type: Article
• Publication Date: Oct 2, 2006
• Deposit Date: Jun 9, 2022
• Journal: Inorganic Chemistry
• Print ISSN: 0020-1669
• Publisher: American Chemical Society
• Peer Reviewed: Peer Reviewed
• Volume: 45
• Issue: 20
• Pages: 8288-8296
• DOI: https://doi.org/10.1021/ic0611591
• Public URL: https://hull-repository.worktribe.com/output/3622666