Convergent/divergent synthesis and photophysical studies of alternating benzene-furan oligoaryls from substituted propargylic dithioacetals.
A range of oligoaryls that contain alternating benzene-furan rings is synthesized by a rapid convergent/divergent method from the annulation of a propargylic dithioacetal and an aldehyde with a propargylic dithioacetal moiety as a substituent. These oligomers are fairly soluble in a range of organic solvents and can be easily purified by reprecipitation. The substituents on the furan rings can be varied according to the substituents in the starting propargylic dithioacetals. This route provides a useful procedure for the synthesis of alternating benzene-furan oligomers without repeated units. These furan-containing oligoaryls are highly fluorescent in the visible region and are electrochemically active. The band gaps of these oligomers appear to be less sensitive towards changes in conjugation length than those of oligofurans.
Chou
Chih-Ming
CM
Department of Chemistry, National Taiwan University, Taipei, 106, Taiwan.
Chen
Wei-Qiang
WQ
Chen
Jia-Hong
JH
Lin
Cheng-Lan
CL
Tseng
Jui-Chang
JC
Lee
Chin-Fa
CF
Luh
Tien-Yau
TY