Synlett 2018; 29(08): 1014-1019
DOI: 10.1055/s-0036-1591766
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Push-Pull Phenazines Possessing pH-Responsive Absorption Spectra and their Application in Selective Detection of Fe3+ Ions and Aromatics

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
,
Apeksha Ashok Phadte
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
,
P. Bhavana
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
› Author Affiliations
SB would like to acknowledge research support from Science & Engineering Research Board, Department of Science & Technology (DST‑SERB), Govt. of India for a generous research grant (SERB/F/519/2014-15) under the Young Scientist Scheme.
Further Information

Publication History

Received: 24 October 2017

Accepted after revision: 29 January 2018

Publication Date:
27 February 2018 (online)


Abstract

Phenazines bearing electron-donor and electron-acceptor groups with high pH-sensing behavior were synthesized in moderate to good yields. Theoretical calculations on the frontier molecular orbitals and experimental oxidation potential measurements under variable pH values provide evidence for extensive internal charge transfer at high pH value. The well-known strong affinity of the catecholate moiety present in our phenazines is utilized for spectrophotometric detection of Fe3+ ion. Fluorescence-quenching behavior of the prepared phenazines is utilized for detection and distinction of electron-rich and electron-poor aromatics.

Supporting Information

 
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