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

Parmeshwar Solanke; Filip Bureš; Olřich Pytela; Jiří Kulhánek; Zdeňka Padělková

doi:10.1055/s-0033-1339664

Synthesis, Inhaltsverzeichnis

Synthesis 2013; 45(21): 3044-3051
DOI: 10.1055/s-0033-1339664

paper

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

Parmeshwar Solanke

^aInstitute 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*

^aInstitute 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

^aInstitute 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

^aInstitute 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

^bDepartment of General and Inorganic Chemistry, Faculty of Chemical Technology, University of Pardubice, Studentská 573, Pardubice, 53210, Czech Republic

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Abstract

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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.

Key words

chromophores - cross-coupling - conjugation - UV/Vis spectroscopy - theoretical calculations

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Referenzen

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