Synthesis of fluorescent molecular switches based on porphyrinoids covalently linked with redox active ligands

Nisa, Kharu; Mishra, Gaurav Kumar; Thirumal, M.; Chauhan, S. M. S.

doi:10.1016/j.molstruc.2021.131407

Cited by 3 publications

(2 citation statements)

References 60 publications

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“…Organic molecules, porphyrins, and their derivatives are potential candidates for NLO applications due to their extended π-conjugation, low HOMO–LUMO gap, and fast optical response. ,,− The third-order optical nonlinearities of these copper corroles are studied in dimethylformamide (DMF) solution using the femtosecond single beam pulse propagation (Z-scan) technique. In the Z-scan, an 800 nm (120 fs, 1 kHz) femtosecond laser pulse is focused using a convex lens, and the transmittance through the sample is recorded for each z position.…”

Section: Resultsmentioning

confidence: 99%

Ultrafast Dynamics and Strong Two-Photon Absorption Properties of Nonplanar β-Functionalized “Push–Pull” Copper Corroles with a Mixed Substituent Pattern

et al. 2022

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A new series of nonplanar and unsymmetrically βfunctionalized "push−pull" copper corroles, CuTPC(CHO)R 7 [R = H, Br, Ph, Me, or 2-thienyl (Th)], were synthesized and characterized to elucidate the effect of β-functionalization and nonplanarity on the photophysical, redox, and nonlinear optical (NLO) properties on the corrole ring. The synthetic route to unsymmetrically β-octasubstituted copper corroles includes bromination of CuTPC(CHO) to get CuTPC(CHO)Br 7 in 80% yield, which was further subjected to the Pd-catalyzed Suzuki reaction. CuTPC(CHO)Br 7 exhibited a large red shift in the Soret band (Δλ max = 35−40 nm) and both the Q bands (Δλ max = 10−50 nm), as compared to CuTPC and CuTPC(CHO). CuTPC(CHO)Br 7 was 510 and 290 mV anodically shifted in the first oxidation and the first reduction compared to CuTPC owing to the strong −I effect of CHO and Br groups. Density functional theory studies revealed that all the β-octasubstituted copper corroles exhibited highly nonplanar saddle-shape conformation of the corrole ring. Very high torsional saddling was observed for CuTPC(CHO)Th 7 (79−83°) than that for CuTPC (49−53°), even larger than that for CuTPCBr 8 (67−70°). Femtosecond laser-induced third-order NLO studies from these copper corroles showed strong twophoton absorption cross-sections (0.48−6.98 × 10 4 GM) and self-focusing-type positive nonlinear refraction behavior. The observed structure-dependent two-photon absorption coefficients (β) are in the range of ∼2.7−20.9 × 10 −12 m/W, and the n 2 values are in the range of ∼0.64−6.45 × 10 −18 m 2 /W. The present results may facilitate a new window for these copper corroles in nonlinear optical devices, femtosecond optical limiters, and many other ultrafast photonic applications.

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Section: Resultsmentioning

confidence: 99%

Ultrafast Dynamics and Strong Two-Photon Absorption Properties of Nonplanar β-Functionalized “Push–Pull” Copper Corroles with a Mixed Substituent Pattern

et al. 2022

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“…48 The applications of hexa-cata-hexabenzocoronene have been rarely reported to date. Porphyrin conjugates based on hexabenzocoronene display photochromism, are capable of showing absorption in NIR of electromagnetic spectrum [49][50][51] and are anticipated to be viable candidates for PDT and magnetic resonance imaging. Multifunctionalized fluorescent dyes are of great interest for photo based cancer theranostics.…”

Section: Rsc Medicinal Chemistry Reviewmentioning

confidence: 99%

Applications of supramolecular assemblies in drug delivery and photodynamic therapy

Nisa,

Lone,

Arif

et al. 2023

RSC Med. Chem.

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Click Chemistry ‐ Inspired Synthesis of Porphyrin Hybrid Glycodendrimers as Fluorescent Sensor for Cu(II) Ions

et al. 2022

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An expeditious and modular CuAAC ‘click’ protocol has been exploited for the construction of porphyrin cored hybrid glycodendrimers of G1 and G2 generation. The developed porphyrin hybrid glycodendrimers were characterized using extensive spectral analysis including NMR (1H, 13C, and 19F), MS, MALDI‐TOF, IR, and SEC datas and evaluated for their sensing ability for a range of metal ions, where they displayed notable sensing for Cu(II) ion with solvatochromism properties.

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Synthesis of fluorescent molecular switches based on porphyrinoids covalently linked with redox active ligands

Cited by 3 publications

References 60 publications

Ultrafast Dynamics and Strong Two-Photon Absorption Properties of Nonplanar β-Functionalized “Push–Pull” Copper Corroles with a Mixed Substituent Pattern

Ultrafast Dynamics and Strong Two-Photon Absorption Properties of Nonplanar β-Functionalized “Push–Pull” Copper Corroles with a Mixed Substituent Pattern

Applications of supramolecular assemblies in drug delivery and photodynamic therapy

Click Chemistry ‐ Inspired Synthesis of Porphyrin Hybrid Glycodendrimers as Fluorescent Sensor for Cu(II) Ions

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