Synlett 2016; 27(05): 799-804
DOI: 10.1055/s-0035-1560991
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis and Optical Properties of 1,4- and 1,2-Dicyanodibenzodioxins Possessing Donor–π-Acceptor Architecture

Subhadeep Banerjee*
a   Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India   eMail: subhadeepb@goa.bits-pilani.ac.in
,
Anjan Chattopadhyay
a   Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India   eMail: subhadeepb@goa.bits-pilani.ac.in
,
Praveen Saini
a   Birla Institute of Technology and Science-Pilani, K.K. Birla Goa Campus, NH-17B Bypass, Zuarinagar, Goa 403726, India   eMail: subhadeepb@goa.bits-pilani.ac.in
,
Keisham Sarjit Singh
b   Bioorganic Chemistry Laboratory, CSIR-National Institute of Oceanography, Dona Paula, Goa 403004, India
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Publikationsverlauf

Received: 02. September 2015

Accepted after revision: 20. Oktober 2015

Publikationsdatum:
09. Dezember 2015 (online)


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Abstract

The synthesis and photophysical characterization of isomeric 1,4-and 1,2-dicyanodibenzodioxins is reported. The molecules exhibit optical spectra in the visible region and possess large (ca. 100 nm) Stokes shifts. The synthetic protocol is simple and high-yielding and the presence of replaceable fluorine atoms on the activated dibenzodioxin moiety provides the opportunity for further transformation towards molecules bearing push–pull architecture.

Supporting Information