Synthesis and spectroscopic properties of meso-substituted quinoxalinoporphyrins

Sharma, Satyasheel; Nath, Mahendra

doi:10.1039/c1nj20248k

Cited by 17 publications

(9 citation statements)

References 31 publications

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“…Such hybrid compounds may prove useful for pharmacological studies or in the development of new phototherapeutic agents. Therefore, in continuation of our efforts towards the synthesis of diverse porphyrin analogues [38–41] through peripheral functionalization of easily accessible meso -tetraarylporphyrins, we now report herein the first synthesis and spectroscopic characterization of a novel series of dihydro-1,3-oxazinoporphyrins.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

Sharma¹,

Nath²

2013

Beilstein J. Org. Chem.

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SummaryNovel dihydro-1,3-oxazinoporphyrins and naphtho[e]bis(dihydro-1,3-oxazinoporphyrin) derivatives, in which the porphyrin macrocycle is covalently linked to the dihydro-1,3-oxazine ring system were successfully synthesized from 5-(4-aminophenyl)-10,15,20-triphenylporphyrin in good yields. The structures of the target products were established on the basis of spectral data and elemental analyses.

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Section: Introductionmentioning

confidence: 99%

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

Sharma¹,

Nath²

2013

Beilstein J. Org. Chem.

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“…The electron transfer reductions of quinoxalinoporphyrins can involve the central metal ion, the porphyrin macrocycle, or the fused quinoxaline group(s), all of which are redox active. − The sites of electron transfer, whether at the metal, at the macrocycle, or at the quinoxaline (Q) part of the molecule, are important factors to know and control since the electron transfer reactivity of these metalloporphyrins are directly related to their possible applications in photovoltaics , and molecular electronics. − Among the quinoxalinoporphyrins previously examined are the gold(III) derivatives which have been shown to undergo three or more one-electron reductions in nonaqueous media. − ,, The first reduction is in almost all cases a metal-centered Au III /Au II process and leads to formation of an Au(II) porphyrin which can be further reduced at more negative potentials to give stepwise an Au(II) porphyrin π-anion radical and dianion under the given solution conditions. Further reductions beyond that of the Au(II) porphyrin dianion are also possible.…”

Section: Introductionmentioning

confidence: 99%

Unusual Multi-Step Sequential Au^III/Au^II Processes of Gold(III) Quinoxalinoporphyrins in Acidic Non-Aqueous Media

Zhu

Fang

et al. 2011

Inorg. Chem.

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The electrochemistry of gold(III) mono- and bis-quinoxalinoporphyrins was examined in CH(2)Cl(2) or PhCN containing 0.1 M tetra-n-butylammonium perchlorate (TBAP) before and after the addition of trifluoroacetic acid to solution. The investigated porphyrins are represented as Au(PQ)PF(6) and Au(QPQ)PF(6), where P is the dianion of the 5,10,15,20-tetrakis(3,5-di-tert-butylphenyl)porphyrin and Q is a quinoxaline group fused to a β,β'-pyrrolic position of the porphyrin macrocycle; in Au(QPQ)PF(6) there is a linear arrangement where the quinoxalines are fused to pyrrolic positions that are opposite each other. The porphyrin without the fused quinoxaline groups, Au(P)PF(6), was also investigated under the same solution conditions. In the absence of acid, all three gold(III) porphyrins undergo a single reversible Au(III)/Au(II) process leading to the formation of a Au(II) porphyrin which can be further reduced at more negative potentials to give stepwise the Au(II) porphyrin π-anion radical and dianion, respectively. However, in the presence of acid, the initial Au(III)/Au(II) processes of Au(PQ)PF(6) and Au(QPQ)PF(6) are followed by an internal electron transfer and protonation to regenerate new Au(III) porphyrins assigned as Au(III)(PQH)(+) and Au(III)(QPQH)(+). Both protonated gold(III) quinoxalinoporphyrins then undergo a second Au(III)/Au(II) process at more negative potentials. The electrogenerated monoprotonated monoquinoxalinoporphyrin, Au(II)(PQH), is then further reduced to its π-anion radical and dianion forms, but this is not the case for the monoprotonated bis-quinoxalinoporphyrin, Au(II)(QPQH), which accepts a second proton and is rapidly converted to Au(III)(HQPQH)(+) before undergoing a third Au(III)/Au(II) process to produce Au(II)(HQPQH) as a final product. Thus, Au(P)PF(6) undergoes one metal-centered reduction while Au(PQ)PF(6) and Au(QPQ)PF(6) exhibit two and three Au(III)/Au(II) processes, respectively. These unusual multistep sequential Au(III)/Au(II) processes were monitored by thin-layer spectroelectrochemistry and a reduction/oxidation mechanism for Au(PQ)PF(6) and Au(QPQ)PF(6) in acidic media is proposed.

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“…In continuation of our efforts to develop synthetic methods for various β-functionalized porphyrins, [28][29][30][31][32][33][34][35][36][37] we present herein a La(OTf)3-catalyzed synthetic protocol for the preparation of nickel(II) 2-imino-5,10,15,20-tetraphenylporphyrins, which have been employed as precursors to construct a new series of β-substituted nickel(II) porphyrin-thiazolidinone hybrids. The synthetic details and spectral properties of newly prepared porphyrins are discussed in this report.…”

Section: Introductionmentioning

confidence: 99%

La(OTf)3-Catalyzed Synthesis of Nickel(II) β-Iminoporphyrins and Their Conversion to β-Substituted Porphyrin-Thiazolidinone Hybrids

Bhatt¹,

Singh²,

Tiwari³

et al. 2021

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Two diverse series of nickel(II) β-iminoporphyrins were prepared in good yields by the reaction of corresponding 2-formyl-and 2-amino-5,10,15,20-tetraphenylporphyrins with primary amines and aldehydes, respectively, in toluene containing a catalytic amount of La(OTf)3 under reflux conditions. These 2-iminoporphyrins further served as precursors to construct novel nickel(II) complexes of β-substituted porphyrinic thiazolidinones in moderate yields on reaction with mercaptoacetic acid in refluxing toluene. All the synthesized porphyrins have been characterized on the basis of spectral data analysis.

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Synthesis and spectroscopic properties of meso-substituted quinoxalinoporphyrins

Cited by 17 publications

References 31 publications

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

Unusual Multi-Step Sequential Au^III/Au^II Processes of Gold(III) Quinoxalinoporphyrins in Acidic Non-Aqueous Media

La(OTf)3-Catalyzed Synthesis of Nickel(II) β-Iminoporphyrins and Their Conversion to β-Substituted Porphyrin-Thiazolidinone Hybrids

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Synthesis and spectroscopic properties of meso-substituted quinoxalinoporphyrins

Cited by 17 publications

References 31 publications

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

Synthesis of meso-substituted dihydro-1,3-oxazinoporphyrins

Unusual Multi-Step Sequential AuIII/AuII Processes of Gold(III) Quinoxalinoporphyrins in Acidic Non-Aqueous Media

La(OTf)3-Catalyzed Synthesis of Nickel(II) &beta;-Iminoporphyrins and Their Conversion to &beta;-Substituted Porphyrin-Thiazolidinone Hybrids

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Unusual Multi-Step Sequential Au^III/Au^II Processes of Gold(III) Quinoxalinoporphyrins in Acidic Non-Aqueous Media

La(OTf)3-Catalyzed Synthesis of Nickel(II) β-Iminoporphyrins and Their Conversion to β-Substituted Porphyrin-Thiazolidinone Hybrids