PMID: 11902891Mar 21, 2002Paper

Supramolecular chirogenesis in zinc porphyrins: equilibria, binding properties, and thermodynamics

Journal of the American Chemical Society
Victor V BorovkovYoshihisa Inoue

Abstract

Complexation mechanism, binding properties and thermodynamic parameters of supramolecular chirality induction in the achiral host molecule, syn (face-to-face conformation) ethane-bridged bis(zinc porphyrin), upon interaction with chiral monoamine and monoalcohol guests have been studied by means of the UV-vis, CD, (1)H NMR, and ESI MS techniques. It was found that the chirogenesis process includes three major equilibria steps: the first guest ligation to a zinc porphyrin subunit of the host (K(1)), syn to anti conformational switching (K(S)), and further ligation by a second guest molecule to the remaining ligand-free zinc porphyrin subunit (K(2)), thus forming the final bis-ligated species possessing supramolecular chirality. The validity of this equilibria model is confirmed by the excellent match between the calculated and experimentally observed spectral parameters of the bis-ligated species. The second ligation proceeds in a cooperative manner as K(2) > K(1) for all supramolecular systems studied, regardless of the structure of the chiral ligand used. The binding properties are highly dependent on the nature of the functional group (amines are stronger binders than alcohols) and on the structure of the chiral guests (prima...Continue Reading

References

Jul 18, 2001·Journal of the American Chemical Society·T YamaguchiT Ito
Jul 18, 2001·Journal of the American Chemical Society·A TanataniJ S Moore
Jul 18, 2001·Journal of the American Chemical Society·H NakashimaM Motonaga
Jul 18, 2001·Journal of the American Chemical Society·C Y LiB Lotz
Jul 18, 2001·Journal of the American Chemical Society·H FenniriJ G Stowell
Jan 5, 2001·Angewandte Chemie·Andreas J TerpinKenneth N Raymond

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Citations

Mar 12, 2005·Organic Letters·Victor V BorovkovYoshihisa Inoue
Aug 27, 2005·Organic Letters·Tadashi EmaTakashi Sakai
Nov 26, 2008·Chemical Communications : Chem Comm·Juan EtxebarriaPablo Ballester
Oct 8, 2009·Chemical Communications : Chem Comm·Nina BerovaGloria Proni
Jun 19, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Michiya FujikiAyako Nakao
Feb 26, 2016·Journal of the American Chemical Society·Yoshimasa SuzukiEiji Yashima
May 18, 2016·Chemical Reviews·Hua Lu, Nagao Kobayashi
Jun 23, 2015·Dalton Transactions : an International Journal of Inorganic Chemistry·Xianshi FangChuanjiang Hu
Apr 4, 2018·Dalton Transactions : an International Journal of Inorganic Chemistry·Tingting HuJian-Ping Lang
Oct 16, 2004·Angewandte Chemie·Victor V BorovkovYoshihisa Inoue
May 10, 2005·Journal of Peptide Science : an Official Publication of the European Peptide Society·Lukás PalivecKarel Volka
Feb 25, 2014·Physical Chemistry Chemical Physics : PCCP·Shinsuke IshiharaKatsuhiko Ariga
Mar 30, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Jiaxun JiangYong Wang
Mar 24, 2009·Chemical Reviews·Irina BeletskayaChristine Stern
Dec 22, 2007·Chemical Reviews·Guy A HemburyYoshihisa Inoue
Mar 23, 2017·Langmuir : the ACS Journal of Surfaces and Colloids·Fan XieMing Hua Liu
Mar 11, 2006·The Journal of Physical Chemistry. B·Ludovico ValliSalvatore Sortino

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