Experimental and Theoretical Studies on Oligomer Formation of N‐Confused Porphyrin–Zinc(II) Complexes

Toganoh, Motoki; Harada, Naoyuki; Morimoto, Tatsuki; Furuta, Hiroyuki

doi:10.1002/chem.200600776

Cited by 26 publications

(18 citation statements)

References 67 publications

(16 reference statements)

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“…18). 43,114,115 Meanwhile, X-ray crystal structures of E-dimers are also reported for [Fe II (NCP 2À )] 2 and [Mn II (NCP 2À )] 2 (Fig. 19).…”

Section: Ni Pd and Pt Complexes (Group 10)mentioning

confidence: 86%

“…39 Partially meso-unsubstituted NCPs are also prepared with [2+2] or [3+1] condensation reactions. [40][41][42][43] b-Alkyl N-confused porphyrins b-Alkyl NCPs are reasonably prepared by the MacDonaldtype [2+2] condensation reaction by the Dolphin's group (Scheme 4) 44 and by the [3+1] condensation reactions by the Lash's group (Scheme 5). 45 When the a-position of N-confused pyrrole ring is unsubstituted, the yields of NCPs tend to decrease and, in turn, amide-type NCPs are obtained.…”

Section: N-confused Porphinementioning

confidence: 99%

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Blooming of confused porphyrinoids—fusion, expansion, contraction, and more confusion

2012

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This article introduces an overview of progressively developing chemistry of N-confused porphyrin and related macrocycles. Study on confusion results in discovery of fusion and combination with expansion or contraction has provided uniquely important classes of porphyrinoids. Syntheses, properties and coordination chemistry of such porphyrinoids are briefly described. Possibilities in applications are also mentioned.

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“…18). 43,114,115 Meanwhile, X-ray crystal structures of E-dimers are also reported for [Fe II (NCP 2À )] 2 and [Mn II (NCP 2À )] 2 (Fig. 19).…”

Section: Ni Pd and Pt Complexes (Group 10)mentioning

confidence: 86%

Section: N-confused Porphinementioning

confidence: 99%

Blooming of confused porphyrinoids—fusion, expansion, contraction, and more confusion

2012

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“…Particularly, the outward nitrogen atom of the confused pyrrole ring is fascinating in terms of the supramolecular assemblies, affording self-assembled metal complexes through their exterior binding modes (26). For example, treatment of 2 with Zn(II) salts leads to an N-confused porphyrin trimer where three core units are mutually coordinated by the peripheral nitrogen atom and Zn(II) ion (27)(28)(29). Similar coordination modes were seen in the other transition metal complexes of meso-aryl-substituted N-confused porphyrins (23).…”

Section: Introductionmentioning

confidence: 99%

Supramolecular dimeric structures of pyrazole-containing meso-oxo carbaphlorin analogues

Ishida

Fujimoto

Morimoto

et al. 2016

Supramolecular Chemistry

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Synthesis and properties of a novel meso-oxo carbaphlorin analogue embedded with an N-free pyrazole moiety are described. The N-benzyl precursor was prepared by a [3 + 1]-MacDonald condensation of N-benzyl pyrazole dialdehyde and β-alkyl-substituted tripyrrane dicarboxylic acid and subsequent oxidation by ferric chloride. Upon deprotection of the benzyl group, the resulting N-free oxophlorin analogue formed a unique supramolecular dimer through mutual hydrogen bonding interactions between the pyrazole NH and meso-carbonyl group. The assembled behaviour was characterised by various spectroscopies, X-ray crystallographic analysis and vapour pressure osmometry. Under the similar reaction conditions, the condensation of meso-phenyl-substituted tripyrrane derivative afforded an unprecedented tetrapyrrolic macrocycle fused with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone unit at their α-pyrrolic positions. The X-ray crystallographic analysis of the macrocycle revealed a twisted core structure, and nonaromatic nature was elucidated.

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“…[29][30][31][32][33] Toganoh et al calculated the oligomer formation of N-confused zinc-porphyrin complexes. 34 The stable isomers of these oligomers are formed through the coordination of the peripheral nitrogen atoms of one molecule to the metal core of another. To the best of our knowledge, the intermolecular interactions between two porphyrin diacid monomers have not been theoretically studied yet.…”

Section: Introductionmentioning

confidence: 99%

Theoretical study of intermolecular interactions in meso-tetraphenylporphyrin diacid dimer (H4TPPCl2)2

Ding

et al. 2009

Phys. Chem. Chem. Phys.

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The intermolecular interactions between two meso-tetraphenylporphyrin diacid H(4)TPPCl(2) monomers are investigated by density functional theory with the PBE1PBE functional and 6-31G* basis set. Structures of five stable isomers of (H(4)TPPCl(2))(2) are determined. It is found that the interaction (IMHB-1) of Cl with ortho H atoms in two phenyl groups of H(4)TPPCl(2) is unique in that it is the strongest interaction between two H(4)TPPCl(2) monomers. Natural bond orbital analysis is carried out to explain the subtle differences of hydrogen bondings in these isomers. To understand the interactions of water molecule with H(4)TPPCl(2) and (H(4)TPPCl(2))(2), structures of H(4)TPPCl(2) x H(2)O and nine isomers of (H(4)TPPCl(2))(2) x H(2)O are also determined. The binding energy of H(4)TPPCl(2) x H(2)O is 36.47 kJ mol(-1), less than that of the most stable structure of (H(4)TPPCl(2))(2) dimers, 41.59 kJ mol(-1). The dimers containing the special IMHB-1 interactions may be the elementary building blocks for the aggregation of H(4)TPPCl(2), which is supported by the crystal structure of H(4)TPPCl(2).H(2)O x 2CH(3)CN. Thus, study of the interactions between two or a small number of gas molecules can provide important information for understanding the main interactions and stable structures in related condensed-phase systems.

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Experimental and Theoretical Studies on Oligomer Formation of N‐Confused Porphyrin–Zinc(II) Complexes

Cited by 26 publications

References 67 publications

Blooming of confused porphyrinoids—fusion, expansion, contraction, and more confusion

Blooming of confused porphyrinoids—fusion, expansion, contraction, and more confusion

Supramolecular dimeric structures of pyrazole-containing meso-oxo carbaphlorin analogues

Theoretical study of intermolecular interactions in meso-tetraphenylporphyrin diacid dimer (H4TPPCl2)2

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