Synthesis of Tetrathiafulvalene Derivatives with Bromo m-xylyl and Acetulated Glucose Units: Precursors to Tetrathiafulvalene Macrocycles

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Title Synthesis of Tetrathiafulvalene Derivatives with Bromo m-xylyl and Acetulated Glucose Units: Precursors to Tetrathiafulvalene Macrocycles
 
Creator Kristine G Eusebio; Center for Natural Sciences and Ecological Research, Chemistry Department, De La Salle University – Manila
Sheryl Robles-Lontok; Center for Natural Sciences and Ecological Research, Chemistry Department, De La Salle University – Manila
Glenn V Alea; Center for Natural Sciences and Ecological Research, Chemistry Department, De La Salle University – Manila
 
Subject Chemistry
Electroactive macrocycle, Van der Waal's interaction, host-guest interaction
 
Description Two tetrathiafulvalene derivatives: tetrathiafulvalene with two bromo m-xylyl substituents (1) and tetrathiafulvalene with two acetylated bromo-glucopyranosyl substituents (2) were synthesized. The synthesis involved the preparation of the cyanoethyl protected tetrathiafulvalene (10) from zinc complex (6) in five steps. Deprotection of (10) using cesium hydroxide and the reaction of the resulting dithiolate with 2.5 equivalent of α, α' m-xylyldibromide yielded 8.408% of (1), while the addition of 1-bromo-2,3,4-tri-O-acetyl-6- iodoglucopyranoside (13) to deprotected (10) produced (2) in 16.19% yield. The TTF derivatives (1) and (2) could be used as precursors to the synthesis of macrocycles containing phenyl and/or sugar units.Keywords: Electroactive macrocycle, Van der Waal's interaction, host-guest interaction.DOI: 10.3860/jrsce.v3i3.98Journal of Research in Science, Computing and Engineering (JRSCE) Vol.3(3) 2006 12-17
 
Publisher De La Salle University-Manila
 
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Date 2008-05-09
 
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Format application/pdf
 
Identifier http://www.philjol.info/index.php/JRSCE/article/view/98
 
Source Journal of Research in Science, Computing and Engineering; Vol 3, No 3 (2006); 12-17
 
Language en
 
Coverage Philippines