Naslov
Novel geometry polynorbornane scaffolds for chromophore linkage and spacing

Autori
Warrener, Ronald N. ; Margetić, Davor ; Mann, David A. ; Chen, Zhi-Long ; Butler, Douglas N.

Vrsta, podvrsta i kategorija rada
Poglavlja u knjigama, znanstveni

Knjiga
Artificial Photosynthesis: From Basic Biology to Industrial Application

Urednik/ci
Collings, A. F. ; Critchley, C.

Izdavač
Wiley-VCH

Grad
Weinheim

Godina
2005

Raspon stranica
147-166

ISBN
3-527-31090-8

Ključne riječi
Carbonyls, cycloaddition, 1, 3-dipole

Sažetak
Several types of carbonyl p-bonds (aldehydes, aryl-fused ring COs) have been shown to act as dipolarophiles in a [4p+2p] reaction with those 1, 3-dipoles formed by the ring-opening of ester-activated cyclobutene epoxides. This new reaction produced cycloadducts incorporating the CO bond into a rigid polyalicyclic scaffold and positioning the attached chromophore stereoselectively, viz single bond attachment with aldehydes, spiro-fusion with ring-ketones. A selection of chromophore-spacer-chromophore dyads have been prepared in which combinations of chromophores (1, 4-dimethoxynaphthalene, 1, 10-phenanthroline, 3, 6-di(4-pyridyl)pyridazine, anthracene, porphyrins) have been separated by up to 7s-bonds (and more in principle) and related one to the other in novel geometrical orientations. Preliminary results involving cyclic a-diones and cyclic triones as 2p-reagents has considerably improved the range of unsymmetrical dyads available using this COCE coupling protocol ; building sequences involving ninhydrin being especially versatile. Other BLOCK methods for the preparation of mixed chromophore dyads have been reviewed and several new norbornene building BLOCKs described.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA