Difunctionalized N-Confused Porphyrins: Synthesis, Fluorescence, and Electrochemical Studies

Sudipta Das; Naresh Balsukuri; Praseetha E. Kesavan; Iti Gupta

doi:10.1071/CH14383

RESEARCH ARTICLE

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Difunctionalized N-Confused Porphyrins: Synthesis, Fluorescence, and Electrochemical Studies

Sudipta Das ^A , Naresh Balsukuri ^A , Praseetha E. Kesavan ^A and Iti Gupta ^A ^B

+ Author Affiliations

- Author Affiliations

^A Indian Institute of Technology Gandhinagar, VGEC Campus, Chandkheda, Ahmedabad-382424, India.

^B Corresponding author. Email: iti@iitgn.ac.in

Australian Journal of Chemistry 68(6) 896-905 https://doi.org/10.1071/CH14383
Submitted: 14 June 2014 Accepted: 28 August 2014 Published: 18 November 2014

Abstract

Seven di-substituted N-confused porphyrins (NCPs) 9–15 bearing two aryl functional groups (cis-A₂B₂ type) were synthesized in 4–7 % yields via [3+1] approach. The corresponding five 5,10-diaryl-substituted symmetrical tripyrranes 1–5 were prepared and condensed with 2,4-bis(hydroxypentaflurophenyl)pyrrole 6. Two outer N-methyl type A₂B₂ NCPs 14 and 15 were also prepared via a similar approach using a new key precursor 8. All the porphyrins 9–15 were characterized by high-resolution mass spectrometry, NMR, infrared spectroscopy, UV–visible spectroscopy, fluorescence spectroscopy, and cyclic voltammetry. Fluorescence studies of 9–15 showed blue-shifted emission maxima and lower Stokes shifts values when compared with N-confused tetraphenylporphyrin (NCTPP). Electrochemical studies indicated easier oxidation of N-methyl NCPs 14 and 15 when compared with remaining NCPs 9–13.

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Difunctionalized N-Confused Porphyrins: Synthesis, Fluorescence, and Electrochemical Studies

Abstract

References

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