Abstract
(E,E)-1,4-bis(4'-aminostyryl)-2,5-bis(octyloxy)-benzene (6) and its derivative (E,E)-1,4-bis(4'-acetamidostyryl)-2,5-bis(octyloxy)-benzene (7) were synthesized and characterized after alkylation, bromomethylation, Horner-Emmons reaction and reduction from hydroquinone. In order to gain more molecular electronic data, HOMO and LUMO of compound 6 have been calculated by Gaussian 03 W.
Highlights
As we all know, photosynthesis is the most important way on which all the lives in our planet depend directly or indirectly
As shown in Scheme 1, the long alkyl chain ether in the middle phenyl ring can increase the solubility of the chromophores in common solvent considerably, the terminal amino group is a versatile functional group to link with other chromophores, and the O and N substituted ones can elevate the HOMO level
The synthetic strategy employed for the synthesis of 7 was based on the Horner-Emmons reaction
Summary
Photosynthesis is the most important way on which all the lives in our planet depend directly or indirectly. 1,4-bis(Octyloxy)benzene (2): Under Ar, a mixture of hydroquinone (55.0 g, 0.5 mol), KOH (67.2 g, 1.2 mol) and octyl bromide (251.0 g, 1.3 mol) in DMSO (400 mL) was stirred for 48 hours at 80oC. 1,4-bis(Bromomethyl)-2,5-bis(octyloxy)benzene (3): A mixture of 1,4-bis(octyloxy)benzene (6, 33.4 g, 0.1 mol), paraformaldehyde (10.8 g, 0.36 mol), HOAc (80 mL) and HBr (40%, 50 mL) was refluxed for 24 hours; after cooling, the precipitate was collected and washed with water.
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