Synthesis 2012; 44(12): 1928-1934
DOI: 10.1055/s-0031-1291010
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Alkyl-Substituted Tribenzopentaphenes as Versatile Polycondensed Aromatic Hydrocarbon π–π Stacking Building Blocks

Bassam Alameddine
a   Department of Mathematics and Natural Sciences, Gulf University for Science and Technology, Hawally 32093, Kuwait
,
Sofia Martin Caba
b   Chemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739   eMail: titus.jenny@unifr.ch
,
Mauro Schindler
b   Chemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739   eMail: titus.jenny@unifr.ch
,
Titus A. Jenny*
b   Chemistry Department, University of Fribourg, chemin du Musée 9, 1700 Fribourg, Switzerland, Fax: +41(26)3009739   eMail: titus.jenny@unifr.ch
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Publikationsverlauf

Received: 29. Dezember 2011

Accepted after revision: 12. April 2012

Publikationsdatum:
14. Mai 2012 (online)


Abstract

We show the versatile synthesis of four tribenzopentaphene derivatives bearing alkyl side chains at three different positions. Substitutions on two of these positions led to subtle intensity changes at the lines of the blue emission, whereas alkylation in the bay region led to dimerization of the pentaphene derivative, resulting in a distortion of the chromophore geometry and an emission shift to green.