Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: the influence of pi-pi interactions on the molecular structure
M. Larsen et al., Synthesis and conformational studies of a series of 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes: the influence of pi-pi interactions on the molecular structure, J CHEM S P2, (8), 1999, pp. 1749-1757
Citations number
29
Categorie Soggetti
Physical Chemistry/Chemical Physics
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2
Four 5,17-bis-aryl-25,26,27,28-tetrapropoxycalix[4]arenes were prepared via
Negishi, Suzuki and Ullman type couplings [aryl = phenyl (1), 3-bromopheny
l (2), 1-naphthyl (3) and carbazol-9-yl (4)]. The influence of the aryl gro
ups on the structure was studied by X-ray crystallography, NMR, electronic
absorption and fluorescence spectroscopy. The results show a drastic differ
ence in conformation where 1 and 2 prefer to have the substituents away fro
m each other while 3 and 4 have them in close contact. The photophysical pr
operties of 3 and 4 exhibited a very solvent dependent fluorescence.