Synthesis, Crystal Structure, and Nonlinear Optical Behavior of β-Unsubstituted meso−meso E-Vinylene-Linked Porphyrin Dimers

Frampton, Michael J.; Akdas, Huriye; Cowley, Andrew R.; Rogers, Joy E.; Slagle, Jonathan E.; Fleitz, Paul A.; Drobizhev, Mikhail; Rebane, and Aleksander; Anderson, Harry L.

doi:10.1021/ol0520525

Cited by 90 publications

(99 citation statements)

References 26 publications

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“…[50c ,d] As before, alkynyl substituted porphyrins [53b,118] and porphyrin dimers with conjugating bridges [83] have found interest in OL studies. Comprehensive data are available for a series of metal complexes of the symmetric porphyrin 27.…”

Section: Chcl 3 129mentioning

confidence: 98%

“…[119,66a] A typical example on porphyrin dimers are the recent studies performed by Anderson and co-workers on 75. [83] Several studies have addressed the changes incurred upon inclusion of chromophores into other materials. For Zn II TPP it was shown that its incorporation into polymer films does not change the nonlinear refraction compared to in solution but that the material exhibits better photostability.…”

Section: Chcl 3 129mentioning

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: Chcl 3 129mentioning

confidence: 98%

Section: Chcl 3 129mentioning

confidence: 99%

Nonlinear Optical Properties of Porphyrins

et al. 2007

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“…The selection of bonding sites can be important. For example, a structure with vinylene-meso-bridged porphyrin dimers exhibits a large electronic interaction [51], in contrast to β- Figure 16. Schematic representation of dipole moment switching in a ferroelectric porphyrin polymer.…”

Section: Ethyne-bridged Multiporphyrinsmentioning

confidence: 99%

“…The selection of bonding sites can be important. For example, a structure with vinylene-meso-bridged porphyrin dimers exhibits a large electronic interaction [51], in contrast to β-bridged analogs, which allow twisting of the macrocycles out of conjugation. The vinylene-meso-bridged structure also shows a substantial non-linear optical effect.…”

Section: Ethyne-bridged Multiporphyrinsmentioning

confidence: 99%

Structural Aspects of Porphyrins for Functional Materials Applications

2017

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Porphyrinic compounds comprise a diverse group of materials which have in common the presence of one or more cyclic tetrapyrroles known as porphyrins in their molecular structures. The resulting aromaticity gives rise to the semiconducting properties that make these compounds of interest for a broad range of applications, including artificial photosynthesis, catalysis, molecular electronics, sensors, non-linear optics, and solar cells. In this brief review, the crystallographic attributes of porphyrins are emphasized. Examples are given showing how the structural orientations of the porphyrin macrocycle, and the inter-porphyrin covalent bonding present in multiporphyrins influence the semiconducting properties. Beginning with porphine, the simplest porphyrin, we discuss how the more complex structures that have been reported are described by adding peripheral substituents and internal metalation to the macrocycles. We illustrate how the conjugation of the π-bonding, and the presence of electron donor/acceptor pairs, which are the basis for the semiconducting properties, are affected by the crystallographic topology.

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“…meso-meso-Conjugated porphyrin dimer [27] and trimer [28] without a linker were synthesized using Suzuki coupling, the same approach was used for the synthesis of dimers with face-to-face organized porphyrin units attached to aromatic linkers, [29] as well as for a linear trimer. [30] Stille coupling was used for the synthesis of various porphyrin dimers, [31,32] especially for the derivatives with long polyene systems. [33] Heck and Sonogashira reactions are also widely employed for the synthesis of bisporphyrin compounds with different linkers including acetylenic fragments, [34] the latter approach was helpful in the synthesis of porphyrin trimers as well.…”

Section: Introductionmentioning

confidence: 99%