Push-pull porphyrins as nonlinear optical materials

Suslick, Kenneth S.; Chen, Chin‐Ti; Meredith, G. R.; Cheng, Lap Tak

doi:10.1021/ja00043a055

Cited by 174 publications

(118 citation statements)

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“…[55] Suslick and co-workers synthesized a series of porphyrins containing both nitro and amino donor and acceptor substituents 28a-d obtained by the partial reduction of the nitro groups of 5,10,15,20-tetrakis(pnitrophenyl)porphyrin. Similar compounds were also prepared by standard acid-catalyzed mixed condensations (e.g., 29) of two different aldehydes with pyrrole.…”

Section: Asymmetric Porphyrinsmentioning

confidence: 99%

“…[55] Based on the theory that organic molecules with strong electron donor and electron acceptor groups that are connected by a large conjugated p-electron system should have high b values, they investigated meso-substituted porphyrins with both nitro and amino donor and acceptor substituents. EFISH studies in chloroform at 1910 nm gave b values for compounds 28a and 28d of 30 × 10 -30 and 20 × 10 -30 esu, respectively; moderately high compared to other organic molecules at that time.…”

Section: Second-order Nlo Effects In Porphyrinsmentioning

confidence: 99%

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Nonlinear Optical Properties of Porphyrins

et al. 2007

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Porphyrins and phthalocyanines have outstanding chemical and thermal stability. The macrocyclic structure and chemical reactivity of tetrapyrroles offers architectural flexibility and facilitates the tailoring of chemical, physical and optoelectronic parameters. The specific optical properties of the tetrapyrrole macrocycle combined with the synthetic methodologies now available and the already available theoretical and spectroscopic knowledge on their optical behavior make porphyrins a target of choice for this area. They are versatile organic nanomaterials with a rich photochemistry and their excited state properties are easily modulated through conformational design, molecular symmetry, metal complexation, orientation and strength of the molecular dipole moment, size and degree of conjugation of the π‐systems, and appropriate donor‐acceptor substituents. Here we review the structural chemistry and optical properties of recently synthesized porphyrin derivatives that offer potential for nonlinear optical (NLO) applications and complement existing studies on phthalocyanines. Classes of interest include the classic A4 symmetric tetrapyrroles, while optimized systems include push‐pull porphyrins, oligomeric and supramolecular self‐assembled systems, films and nanoparticle systems, and highly conjugated porphyrin arrays.

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Section: Asymmetric Porphyrinsmentioning

confidence: 99%

Section: Second-order Nlo Effects In Porphyrinsmentioning

confidence: 99%

Nonlinear Optical Properties of Porphyrins

et al. 2007

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“…1 The presence of electron withdrawing nitro group(s) in the conjugated positions of porphyrins leads to pronounced intramolecular charge transfer in the excited singlet state.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes

Rajesh¹,

Rahiman²,

Bharathi³

et al. 2010

Bulletin of the Korean Chemical Society

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We have synthesized a series of push-pull porphyrins containing both donor and acceptor substituents at the mesopositions and have examined their spectral and biological properties. The push-pull porphyrins containing both strong donor NH2 and acceptor NO2 at meso-positions, in which donor group condensed with the ligand, (2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formlyphenol (L) to form imine linkages with porphyrin. The Schiff base ligand 5-[4-(2,6-bis(4-methylpiperazine-1-yl-methyl)-4-iminomethylphenol)phenyl]-10,15,20-tris(4-nitrophenyl) porphyrin [an3(TPP)L] can be synthesized from 2,6-bis(4-methylpiperazine-1-yl-methyl)-4-formylphenol (L) and 5-(4-aminophenyl)-10, 15,20-tris(4-nitrophenyl)porphyrin. The push-pull porphyrin [an3(TPP)L] was metallated to get copper, nickel and zinc complexes. The spectral, electrochemical, antibacterial, antifungal and cytotoxicity properties of all the donor-acceptor push-pull porphyrins and their complexes were characterized and studied.

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“…at the water/DCE interface, and compared them to the UV-vis spectra of these two species in the bulk of the two liquids. 369 Although the molecular hyperpolarizability of the symmetrically substituted porphyrins is very small, 370 the adsorbed species give rise to intense SH signals, indicating that its electronic structure at 67 the interface is modified relative to the bulk structure.…”

Section: ) Solute Association and Aggregation May Affect The Spectramentioning

confidence: 99%

Reactivity and Dynamics at Liquid Interfaces

Benjamin¹

2015

Reviews in Computational Chemistry

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Push-pull porphyrins as nonlinear optical materials

Cited by 174 publications

References 1 publication

Nonlinear Optical Properties of Porphyrins

Nonlinear Optical Properties of Porphyrins

Spectroscopic, Redox and Biological Studies of Push-Pull Porphyrins and Their Metal Complexes

Reactivity and Dynamics at Liquid Interfaces

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