Synthesis 2013; 45(21): 3044-3051
DOI: 10.1055/s-0033-1339664
paper
© Georg Thieme Verlag Stuttgart · New York

T-Shaped Push–Pull Chromophores: First Modification of the Indan-1,3-dione-Fused Benzene Ring by Cross-Coupling Reactions

Parmeshwar Solanke
a   Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic   Fax: +420(46)6037068   eMail: filip.bures@upce.cz
,
Filip Bureš*
a   Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic   Fax: +420(46)6037068   eMail: filip.bures@upce.cz
,
Olřich Pytela
a   Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic   Fax: +420(46)6037068   eMail: filip.bures@upce.cz
,
Jiří Kulhánek
a   Institute of Organic Chemistry and Technology, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic   Fax: +420(46)6037068   eMail: filip.bures@upce.cz
,
Zdeňka Padělková
b   Department of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic
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Publikationsverlauf

Received: 04. Juli 2013

Accepted after revision: 01. August 2013

Publikationsdatum:
29. August 2013 (online)


Abstract

A series of eight novel T-shaped chromophores with indan-1,3-dione central acceptor moiety and peripheral N,N-dimethylamino and thiophene donors were synthesized. 4,7-Diiodoindan-1,3-dione was prepared in a straightforward manner from phthalanhydride. Its modification with donors was accomplished by Knoevenagel, Suzuki–Miyaura, and Sonogashira reactions. Target push–pull chromophores were further investigated by X-ray analysis, UV/Vis spectra, and theoretical calculations.

Supporting Information