Synthesis and electrochemical properties of 1,4-dithiafulvenyl-substituted bianthrone molecules with potential application as molecular switches

Autor:	T. Bjoernholm, M. Joergensen, K. Lerstrup, Peter Frederiksen, Kjeld Schaumburg, Kay Brunfeldt, Peter Sommer-Larsen, Klaus Bechgaard
Rok vydání:	1993
Předmět:	Acylation Molecular switch Coupling (electronics) Chemical coupling Absorption spectroscopy Chemistry Organic Chemistry Molecule Electrochemistry Photochemistry Demethylation
Zdroj:	The Journal of Organic Chemistry. 58:2785-2790
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo00062a022
Popis:	Four new 1,4-dithiafulvenyl substituted bianthrones 3 have been prepared with the aim of making a light-activated «molecular switch». Acylation of 10,10'-dimethoxy-9,9'-bianthracene (2) could be controlled to give 3-acyl- or 3,3'-diacyl-10,10'-dimethoxy-9;9'-bianthracenes 4 and 5, respectively. Demethylation and oxidation yielded 2-acylbianthrones 7. Horner-Emmons-type coupling of 4 and 6 with substituted 1,3-dithiole-2-phosphonate esters 8 and 11 gave 1,4-dithiafulvenyl-substituted bianthracenes 9 and 12. Demethylation and oxidation finally gave the 1,4-dithiafulvenyl-substituted bianthrones 3. The electrochemical properties and absorption spectra of these new molecules (3) have been investigated and compared to bianthrone
Databáze:	OpenAIRE
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