Third-order nonlinear optical properties of highly electron deficient, nonplanar push–pull porphyrins: β-nitro-hexa-substituted porphyrins bearing bromo, phenyl, and phenylethynyl groups

Rohal, Renu K.; Banerjee, Dipanjan; Rana, Nivedita; Soma, Venugopal Rao; Sankar, Muniappan

doi:10.1039/d4dt00045e

Dalton Trans.

2024

DOI: 10.1039/d4dt00045e

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Third-order nonlinear optical properties of highly electron deficient, nonplanar push–pull porphyrins: β-nitro-hexa-substituted porphyrins bearing bromo, phenyl, and phenylethynyl groups

Renu K. Rohal,

Dipanjan Banerjee,

Nivedita Rana

et al.

Abstract: β-Heptasubstituted porphyrins [MTPP(NO2)X6; M = 2H, Ni(II), Cu(II), and ZnII; X = Br, Ph, and PE] were synthesized and explored their third-order nonlinear optical (NLO) properties using single-beam Z-scan technique...

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Cited by 3 publications

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Synthesis, Structural, Electrochemical, and DFT Studies of Highly Substituted Nonplanar Ni(II) Porphyrins and Their Intensity-Dependent Third-Order Nonlinear Optical Properties

Bulbul,

Kuriakose,

Komal

et al. 2024

Inorg. Chem.

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We designed and successfully synthesized highly substituted electron-deficient nonplanar Ni(II) porphyrins and their derivatives (1−7) in moderate to good yields. These derivatives were comprehensively characterized by various spectroscopic techniques and single-crystal X-ray diffraction (SCXRD) analysis. SCXRD analysis confirmed the structures of compounds 2, 4, and 7, adopting saddle-shape geometry. These nonplanar porphyrins demonstrated significant bathochromic shifts in their absorption spectra compared to parent NiTPP, attributed to the influence of bulky β-substituents and/or peripheral fusion. π-Extended porphyrins 6 and 7 displayed panchromatic absorption spectra extending into the NIR region. Porphyrins 6 and 7 demonstrated a profound anodic shift (∼400 mV) in their first reduction peak potentials compared to precursor NiTPP(NO 2 )Br 6 . The experimental absorption spectral pattern matches the simulated absorption spectra obtained from TD-DFT studies. The femtosecond laser intensity-dependent third-order nonlinear optical studies revealed that NiDFP(VCN) 2 Br 6 (6) and NiDFP(VCN) 2 (PE) 6 (7) displayed giant optical nonlinearities compared to the other porphyrins. Among all, NiDFP(VCN) 2 Br 6 (6) possessed the highest two-photon absorption coefficient (β) and crosssection (σ TPA ) values in the range of 22−33 × 10 −10 m/W and 3.77−6.95 × 10 6 GM, respectively. These findings suggest that the investigated nonplanar π-extended porphyrins are promising candidates for future optoelectronic applications.

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Synthesis, Structural, Electrochemical, and DFT Studies of Highly Substituted Nonplanar Ni(II) Porphyrins and Their Intensity-Dependent Third-Order Nonlinear Optical Properties

Bulbul,

Kuriakose,

Komal

et al. 2024

Inorg. Chem.

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β-Methoxyphenyl substituted porphyrins: synthesis, characterization and comprehensive spectral, structural, electrochemical and theoretical analysis

Arif,

Kumar,

Chetti

et al. 2024

New J. Chem.

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Influence of a diketopyrrolopyrrole spacer on the ultrafast nonlinear optical properties and excited state dynamics of dimeric zinc porphyrin molecules

Murali,

Biswas,

Nayak

et al. 2025

J. Mater. Chem. C

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Third-order nonlinear optical properties of highly electron deficient, nonplanar push–pull porphyrins: β-nitro-hexa-substituted porphyrins bearing bromo, phenyl, and phenylethynyl groups

Abstract: β-Heptasubstituted porphyrins [MTPP(NO2)X6; M = 2H, Ni(II), Cu(II), and ZnII; X = Br, Ph, and PE] were synthesized and explored their third-order nonlinear optical (NLO) properties using single-beam Z-scan technique...

Cited by 3 publications

References 49 publications

Synthesis, Structural, Electrochemical, and DFT Studies of Highly Substituted Nonplanar Ni(II) Porphyrins and Their Intensity-Dependent Third-Order Nonlinear Optical Properties

Synthesis, Structural, Electrochemical, and DFT Studies of Highly Substituted Nonplanar Ni(II) Porphyrins and Their Intensity-Dependent Third-Order Nonlinear Optical Properties

β-Methoxyphenyl substituted porphyrins: synthesis, characterization and comprehensive spectral, structural, electrochemical and theoretical analysis

Influence of a diketopyrrolopyrrole spacer on the ultrafast nonlinear optical properties and excited state dynamics of dimeric zinc porphyrin molecules

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