TY - JOUR
T1 - Acetylenic cyclodextrins for multireceptor architectures: cups with sticky ends for the formation of extension wires and junctions
AU - Faiz, Jonathan
AU - Spencer, Neil
AU - Pikramenou, Zoe
PY - 2005
Y1 - 2005
N2 - A mono-6-O-propargyl permethylated β-cyclodextrin, 3, has been prepared by two synthetic routes as a versatile building block for the construction of cyclodextrin dimers and trimers with a core junction which is potentially electron conducting. Glaser–Hay coupling of 3 gave β-cyclodextrin dimer 6, and Pd(0)-catalysed coupling allowed the preparation of a cyclodextrin dimer with a 1,4-phenylene bridge, 7, and a cyclodextrin trimer based on a 1,3,5-trisubstituted benzene, 8. All compounds have been fully characterised, and in particular, detailed analysis by 2D NMR spectroscopic techniques has provided useful insight into the identities of the compounds. The detailed full characterisation of mono-3,6-anhydro-heptakis(2,3-O-methyl)-hexakis(6-O-methyl)-β-cyclodextrin, 5, is also described. Product 5 is formed during the methylation of compound 3, and its formation was found to be sensitive to the reaction conditions. The absorption and fluorescence spectra of the phenylene-bridged dimer 7 and trimer 8 are also reported. They show different properties of the excited state based on the different electronic coupling imposed by the phenylene core.
AB - A mono-6-O-propargyl permethylated β-cyclodextrin, 3, has been prepared by two synthetic routes as a versatile building block for the construction of cyclodextrin dimers and trimers with a core junction which is potentially electron conducting. Glaser–Hay coupling of 3 gave β-cyclodextrin dimer 6, and Pd(0)-catalysed coupling allowed the preparation of a cyclodextrin dimer with a 1,4-phenylene bridge, 7, and a cyclodextrin trimer based on a 1,3,5-trisubstituted benzene, 8. All compounds have been fully characterised, and in particular, detailed analysis by 2D NMR spectroscopic techniques has provided useful insight into the identities of the compounds. The detailed full characterisation of mono-3,6-anhydro-heptakis(2,3-O-methyl)-hexakis(6-O-methyl)-β-cyclodextrin, 5, is also described. Product 5 is formed during the methylation of compound 3, and its formation was found to be sensitive to the reaction conditions. The absorption and fluorescence spectra of the phenylene-bridged dimer 7 and trimer 8 are also reported. They show different properties of the excited state based on the different electronic coupling imposed by the phenylene core.
UR - http://www.scopus.com/inward/record.url?scp=29144522147&partnerID=8YFLogxK
U2 - 10.1039/b508607h
DO - 10.1039/b508607h
M3 - Article
C2 - 16294253
VL - 3
SP - 4239
EP - 4245
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 23
ER -