Issue 9, 2008
From the journal:

New Journal of Chemistry

Self-organised nano-arrays of p-phosphonic acid functionalised higher order calixarenes†

Thomas E. Clark,a   Mohamed Makha,*a   Alexandre N. Sobolev,a   Dian Su,b   Henry Rohrs,b   Michael L. Gross,b   Jerry L. Atwoodc  and  Colin L. Raston*a  

* Corresponding authors

a School of Biomedical, Biomolecular and Chemical Sciences, University of Western Australia, 35 Stirling Hwy, Crawley, Australia
E-mail: colin.raston@uwa.edu.au
Fax: (+61) 86488 1005
Tel: (+61) 86488 3045

b Department of Chemistry, Washington University in St. Louis, St. Louis, USA

c Department of Chemistry, University of Missouri-Columbia, Columbia, USA

Abstract

Water-soluble p-phosphonic acid calix[n]arenes (n = 5, 6 or 8) have been synthesized in five steps in overall 68, 66, 67% yield, respectively, by the recently developed procedure for p-phosphonic acid calix[4]arene. The hydrogen bonding prowess of the phosphonic acids dominates their self assembly into nano-arrays in both solution and the gas phase. In DMSO, nano-arrays of p-phosphonic acid calix[6]arene are stable for over 24 h, with the solvent molecules slowly disrupting the hydrogen bonded network affording solvated monomeric units. In the gas phase, nano-arrays of around 20 calixarene units were observed for the p-phosphonic acid calix[n]arenes using MALDI-TOF-MS, and ESI-MS revealed the presence of heteroleptic nano-arrays for a 1 : 1 mixture of p-phosphonic acid calix[4,5]arenes.

Graphical abstract: Self-organised nano-arrays of p-phosphonic acid functionalised higher order calixarenes

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Article information

DOI
https://doi.org/10.1039/B801256C
Article type
Paper
Submitted
23 Jan 2008
Accepted
07 Mar 2008
First published
02 May 2008

New J. Chem., 2008,32, 1478-1483

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Self-organised nano-arrays of p-phosphonic acid functionalised higher order calixarenes

T. E. Clark, M. Makha, A. N. Sobolev, D. Su, H. Rohrs, M. L. Gross, J. L. Atwood and C. L. Raston, New J. Chem., 2008, 32, 1478 DOI: 10.1039/B801256C

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