Chemistry of<i>meso</i>-Aryl-Substituted Expanded Porphyrins: Aromaticity and Molecular Twist

Tanaka, Takayuki; Osuka, Atsuhiro

doi:10.1021/acs.chemrev.6b00371

Cited by 389 publications

(221 citation statements)

References 498 publications

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“…Notably, a troublesome contamination with 5,15-diphenylporphyrin or 5-phenylporphyrin was somehow suppressed, and 1H was obtained in 12% yield [9]. In a similar but slightly modified manner, a condensation reaction of 5,10-bis(pentafluorophenyl)tripyrrane (3b) [10] with 4 followed by oxidation with chloranil gave 5,10-bis(pentafluorophenyl)porphyrin 2H in 17% yield. 2H would be a useful building-block for the construction of designed porphyrin arrays [11].…”

Section: Resultsmentioning

confidence: 99%

1D Columnar stacking structures in the single crystals of 5,10-diarylporphyrin metal complexes

Tanaka

Ueta

Ikeda

et al. 2017

J. Porphyrins Phthalocyanines

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ABSTRACT:A general design of a meso-aryl porphyrin for the formation of a 1D columnar stacking structure in the single crystal state is proposed. We found that 5,10-diphenyl-and 5,10-bis(pentafluorophenyl)porphyrin metal complexes (M = Zn, Ni) can stack in a complementary manner to form a 1D columnar stacking structure in the single crystals, while the corresponding freebase porphyrins displayed herringbone or dimeric orthogonal packing forms. The structural details of the obtained 1D columnar packing structures are discussed in comparison with precedented examples including 5,10-diphenylporphyrin Cu(II) and Ag(II) complexes, 5,10-diphenyl N-confused porphyrin Ag(III) complex and 5,10-bis(pentafluorophenyl)corrole.

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Section: Resultsmentioning

confidence: 99%

1D Columnar stacking structures in the single crystals of 5,10-diarylporphyrin metal complexes

Tanaka

Ueta

Ikeda

et al. 2017

J. Porphyrins Phthalocyanines

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“…The structural dynamic of expanded porphyrins offers terrific platforms to understand the elusive Möbius aromaticity. However, low energy barriers on conformational changes also complicate the study of expanded porphyrins . Several strategies have been introduced to ‘lock’ the conformation of expanded porphyrins.…”

Section: Methodsmentioning

confidence: 99%

2,5‐Thienylene‐Strapped Bicyclic and Tricyclic Expanded Porphyrins

et al. 2019

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An [18]thiaporphyrin[36]dithiaoctaphyrin‐[18]thiaporphyrin tricyclic macrocycle, fused through the 2,5‐thienylene bridging moiety, was isolated during the preparation of 2,5‐thienylene‐strapped [26]hexaphyrin containing o‐dichlorophenyl groups as meso substituents. The spectroscopic data of the 2,5‐thienylene‐strapped [26]hexaphyrin verified contributions of aromaticity from ring currents of both the [18]thiaporphyrin and the [26]hexaphyrin. The crystal structure of the tricyclic macrocycle revealed a distorted [36]dithiaoctaphyrin central core with two [18]thiaporphyrin sidewheels oriented nearly perpendicular to the mean‐plane of dithiaoctaphyrin, implying the existence of independent π‐conjugated systems. Both the absorption maximum at 441 nm and the chemical shifts in the 1H NMR spectrum of the tricyclic macrocycle are dominated by diatropic ring currents of two aromatic [18]thiaporphyrin sidewheels.

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“…Expanded porphyrins are macrocycles containing more than four pyrrolic units, which retain the extended conjugation features as porphyrins. They present a core expansion that produces structures with novel spectral and electronic features …”

Section: Introductionmentioning

confidence: 99%

Quantum chemical studies of porphyrin‐ and expanded porphyrin‐based systems and their potential applications in nanoscience. Latin America research review

Cárdenas-Jirón

Borges-Martínez

Mera‐Adasme

et al. 2018

Int J of Quantum Chemistry

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Porphyrins and expanded porphyrins are fascinating molecular structures, and its wide applicability in different fields of the nanoscience has produced an extensive number of scientific publications. The purpose of this article is to review the research performed on porphyrins and expanded porphyrins in the Latin American region at a theoretical level of quantum chemistry using different methodologies available. The present review is organized considering the most important applications that these molecular systems have found. In this way, we classify the reported works in the following fields studied by the nanoscience: molecular electronics, dye‐sensitized solar cells, and photodynamic therapy. Because of its relevance, we also highlight other reports focused on the topological analysis of the electron density and aromaticity. Current investigation on these topics applied to porphyrin‐ and expanded porphyrin‐based systems and the future perspective in this field are presented.

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Chemistry ofmeso-Aryl-Substituted Expanded Porphyrins: Aromaticity and Molecular Twist

Cited by 389 publications

References 498 publications

1D Columnar stacking structures in the single crystals of 5,10-diarylporphyrin metal complexes

1D Columnar stacking structures in the single crystals of 5,10-diarylporphyrin metal complexes

2,5‐Thienylene‐Strapped Bicyclic and Tricyclic Expanded Porphyrins

Quantum chemical studies of porphyrin‐ and expanded porphyrin‐based systems and their potential applications in nanoscience. Latin America research review

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