Synthesis, Characterization, and Redox Properties of Electron-Deficient Porphyrins with Dual Applications

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Abstract
To investigate the optoelectronic properties of extensively electron-deficient porphyrins, a series of mixed functionalized porphyrins with adjacent nitro (-NO2) and cyano (-CN) functional groups at the β-pyrrolic positions were designed and synthesized via nucleophilic substitution reactions. The synthesized porphyrins were characterized by several spectroscopic techniques and confirmed by single-crystal X-ray diffraction analysis. The electron-deficient nature of porphyrins, as highlighted by their redox properties, makes the macrocycle a selective optical sensor for cyanide ions with a limit of detection of nearly 1 ppm. Furthermore, porphyrins were evaluated for their nonlinear optical responses. Femtosecond laser intensity-dependent third-order nonlinear optical studies were performed using a laser with the following specifications: 800 nm, 120 fs, and 84 MHz at an intensity of 3.0 × 1013 W/m2. Among all analyzed porphyrins, free-base porphyrins exhibited higher nonlinear coefficients compared to metalated porphyrins. Moreover, highly substituted porphyrins showed high nonlinear coefficient values. 3-H2 shows the highest (∼119 × 10-11) two-photon absorption coefficient (β) and the highest negative nonlinear refractive index (-28.2 × 10-17), making it suitable for optical limiting applications.
Funding Information
  • Council of Scientific and Industrial Research, India (01(3058)/21/EMR-II)
  • Anusandhan National Research Foundation (CRG/2020/005958)
  • Ministry of Education, India

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