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

Thomas Clark; Mohamed Makha; Alexandre Sobolev; D. Su; H. Rohrs; M.L. Gross; J.L. Atwood; Colin Raston

doi:10.1039/b801256c

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

Thomas Clark, Mohamed Makha, Alexandre Sobolev, D. Su, H. Rohrs, M.L. Gross, J.L. Atwood, Colin Raston

Research output: Contribution to journal › Article › peer-review

34 Citations (Scopus)

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.

Original language	English
Pages (from-to)	1478-1483
Journal	New Journal of Chemistry
Volume	32
Issue number	9
DOIs	https://doi.org/10.1039/b801256c
Publication status	Published - 2008

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title = "Self-organised nano-arrays of p-phosphonic acid functionalised higher order calixarenes",

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.",

author = "Thomas Clark and Mohamed Makha and Alexandre Sobolev and D. Su and H. Rohrs and M.L. Gross and J.L. Atwood and Colin Raston",

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TY - JOUR

T1 - Self-organised nano-arrays of p-phosphonic acid functionalised higher order calixarenes

AU - Clark, Thomas

AU - Makha, Mohamed

AU - Sobolev, Alexandre

AU - Su, D.

AU - Rohrs, H.

AU - Gross, M.L.

AU - Atwood, J.L.

AU - Raston, Colin

PY - 2008

Y1 - 2008

N2 - 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.

AB - 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.

U2 - 10.1039/b801256c

DO - 10.1039/b801256c

M3 - Article

SN - 1144-0546

VL - 32

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EP - 1483

JO - New Journal of Chemistry

JF - New Journal of Chemistry

IS - 9

ER -

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

Abstract

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