A Schiff-base porphyrin complex with double intramolecular hydrogen bonds

Huang, Wei; Jiang, Jiaxun; Feng, Zhiqiang; Kai, Xiaoxu; Hu, Chuanjiang; Yu, Hong; Yang, Wen

doi:10.1080/00958972.2011.589002

Cited by 9 publications

(3 citation statements)

References 28 publications

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“…They reported upto 99% ee. 42 A Schiff base expanded achiral porphyrin macrocycle that acts as a versatile binucleating ligand was reported by Jonathan L. Sessler et al 43 Porphyrin dimers possessing imine functionalities were also reported. They reported up to 83% ee.…”

Section: Introductionmentioning

confidence: 97%

“…40 A novel porphyrin imine was synthesized via the condensation of 5-(4-aminophenyl)-10,15,20-triphenylporphyrin and ethyl vanillin by Wang Dong et al 41 Wei Huang et al designed a porphyrin with an imine functionality as a model to study intramolecular hydrogen bonding. 42 A Schiff base expanded achiral porphyrin macrocycle that acts as a versatile binucleating ligand was reported by Jonathan L. Sessler et al 43 Porphyrin dimers possessing imine functionalities were also reported. 44 The advancement of asymmetric epoxidation catalyzed by chiral porphyrin schiff base complexes has not been systematically proposed till date.…”

Section: Introductionmentioning

confidence: 97%

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Chiral porphyrin imine manganese complex as catalyst for asymmetric epoxidation of styrene derivatives

Ananthi

Enoch

2019

Chirality

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New chiral porphyrin imine was synthesized from (S)-3-benzyl-2-methyl-4phenylbutanal according to dipyrromethane method using trifluoroacetic acid, BF 3 etherate, and p-chloranil. Manganese complex of this chiral porphyrin imine ligand was used as catalyst in the asymmetric epoxidation of styrene derivatives possessing different substituents. Styrene derivatives possessing electron withdrawing groups gave the corresponding chiral epoxides in high yield up to 98% and ee up to 99%. The mechanism for the catalytic asymmetric epoxidation was also discussed based on transfer of oxygen.KEYWORDS asymmetric epoxidation, asymmetric synthesis, chiral epoxides, chiral porphyrin manganese complexes, epoxidation of styrene

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Section: Introductionmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 97%

Chiral porphyrin imine manganese complex as catalyst for asymmetric epoxidation of styrene derivatives

Ananthi

Enoch

2019

Chirality

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“…Schiff base derivatives of porphyrins appeared to be new promising materials for the fabrication of photovoltaic devices . Considering their photovoltaic applications, there is a potential for the synthesis of different types of Schiff base derivatives of porphyrins, and a number of such derivatives have so far been reported .…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Novel Symmetric Porphyrin Schiff Base Dimers by Solid–Liquid Reaction Methodology

Yaseen

Farooq

Mahmood

et al. 2019

Journal of Heterocyclic Chem

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A new convenient solid–liquid condensation reaction procedure for the synthesis of novel asymmetric and symmetric meso‐tetraarylporphyrin and metalloporphyrin Schiff bases is reported. The condensation reaction between β‐formyl porphyrin or metalloporphyrins and aromatic amines was carried out at solid–liquid interface by using neutral alumina powder as a solid support for β‐formyl porphyrin or metalloporphyrins and absolute ethanol as the carrier solvent for aromatic amines. Six different asymmetric porphyrin/metalloporphyrin Schiff bases were synthesized via solid–liquid interface reaction methodology. The same solid–liquid synthetic methodology was applied for the synthesis of six novel symmetric Schiff base porphyrin/metalloporphyrin dimers. The comparison of UV–visible spectra of porphyrin Schiff base monomers and dimers revealed that some degree of electronic perturbation has occurred upon dimerization as the Soret bands of the monomers underwent peak broadening along with red shifts. Column chromatography and crystallization were used to purify the compounds. Fourier transform infrared, UV–visible, elemental analysis, 1H NMR, and mass spectrometry were used to characterize the newly synthesized compounds.

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Synthesis and spectroscopic characterization of meso-tetra (Schiff-base substituted phenyl) porphyrins and their zinc complexes

Lin

et al. 2013

Dyes and Pigments

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A Schiff-base porphyrin complex with double intramolecular hydrogen bonds

Cited by 9 publications

References 28 publications

Chiral porphyrin imine manganese complex as catalyst for asymmetric epoxidation of styrene derivatives

Chiral porphyrin imine manganese complex as catalyst for asymmetric epoxidation of styrene derivatives

Synthesis of Novel Symmetric Porphyrin Schiff Base Dimers by Solid–Liquid Reaction Methodology

Synthesis and spectroscopic characterization of meso-tetra (Schiff-base substituted phenyl) porphyrins and their zinc complexes

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