TY - JOUR
T1 - Self-organised nano-arrays of p-phosphonic acid functionalised higher order calixarenes
AU - Clark, Thomas E.
AU - Makha, Mohamed
AU - Sobolev, Alexandre N.
AU - Su, Dian
AU - Rohrs, Henry
AU - Gross, Michael L.
AU - Atwood, Jerry L.
AU - Raston, Colin L.
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.
UR - http://www.scopus.com/inward/record.url?scp=52449093309&partnerID=8YFLogxK
U2 - 10.1039/b801256c
DO - 10.1039/b801256c
M3 - Article
AN - SCOPUS:52449093309
SN - 1144-0546
VL - 32
SP - 1478
EP - 1483
JO - New Journal of Chemistry
JF - New Journal of Chemistry
IS - 9
ER -