3-D Cryptand Like Normal and Doubly N-Confused Calixbenzophyrins: Synthesis and Structural Studies

Palepu, Narasinga Rao; Adinarayana, B.; Murugavel, Muthuchamy; Garima, Kumari; Chitranshi, Sangya; Srinivasan, A.

doi:10.1021/acs.orglett.1c00506

Cited by 3 publications

(9 citation statements)

References 34 publications

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“…Confusion was also found in 3-D cages. 502 When tris-(pyrrolylmethyl)benzene 610 was condensed with pentafluorobenzaldehyde 36a, 3-D cryptant-like calixbenzophyrin 611 was obtained in 25% yield (Scheme 223, top). Meanwhile, condensation of N-confused tris(pyrrolylmethyl)benzene 612 afforded doubly N-confused calixbenzophyrin 613 in 24% yield (Scheme 223, bottom).…”

Section: N-confused Pyriporphyrinsmentioning

confidence: 99%

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Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

Toganoh

Furuta

2022

Chem. Rev.

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Confusion is a novel concept of isomerism in porphyrin chemistry, delivering a steady stream of new chemistry since the discovery of N-confused porphyrin, a porphyrin mutant, in 1994. These days, the number of confused porphyrinoids is increasing, and confusion and associated fusion are found in various fields such as supramolecular chemistry, materials chemistry, biological chemistry, and catalysts. In this review, the birth and growth of confused porphyrinoids in the last three decades are described.

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Section: N-confused Pyriporphyrinsmentioning

confidence: 99%

“…Confusion was also found in 3-D cages . When tris(pyrrolylmethyl)benzene 610 was condensed with pentafluorobenzaldehyde 36a , 3-D cryptant-like calixbenzophyrin 611 was obtained in 25% yield (Scheme , top).…”

Section: Miscellaneous N-confused and N-fused Compoundsmentioning

confidence: 99%

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

Toganoh

Furuta

2022

Chem. Rev.

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“…Srinivasan and co-workers recently reported a cryptand-like calixbenzophyrin and its doubly N-confused analogue utilizing acid catalyzed condensation reaction. [20] This approach of condensation to build a bicyclic cage is different from MacDonald condensation (discussed earlier). Upon treatment of the 1,3,5-tris[1-(pyrrolyl)-1,1-(diethyl)methyl]-benzene 15 and its N-confused isomer 16 with pentafluorobenzaldehyde in-dependently in the presence of TFA, followed by DDQ oxidation, gave two structural isomers 17 and 18 (Scheme 4).…”

Section: Acid Catalyzed Condensation Approach: Cryptands With Phenyl ...mentioning

confidence: 99%

“…Srinivasan and co‐workers recently reported a cryptand‐like calixbenzophyrin and its doubly N‐confused analogue utilizing acid catalyzed condensation reaction [20] . This approach of condensation to build a bicyclic cage is different from MacDonald condensation (discussed earlier).…”

Section: Acid Catalyzed Condensation Approach: Cryptands With Phenyl ...mentioning

confidence: 99%

Pyrrole‐Based Cryptand‐Like Cages: A Critical Overview of Synthetic Strategies and Applications

et al. 2022

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Pyrrole-based cryptand-like cages are important owing to their three-dimensional cavities together with three open crevices or clefts. The polar pyrrole subunits in the cages preorganize themselves to construct rigid and shape persistent molecular frameworks. Both the inner voids (cavity and cleft) are accessible to various guests such as metal ions, anions and, neutral molecules. The pyrrole ring offers hydrogen bond donor NH groups and its π-electrons to bind anions or neutral molecules, whereas sigma donation of pyrrolides stabilizes metal ions. In addition, the orientation of bridgehead positions of the cryptand molecules along with specific conformations of the pyrrole rings and/or connecting arms dictate the size of available void space which is directly related to the selectivity for specific guest molecules to be recognized. Thus, the cages have attracted attention in recent times for the development of supramolecular chemistry. In this review, we summarize different synthetic procedures of laterally symmetrical cryptand-like molecules, their structures, and applications in diverse aspects.

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“…[5] Subtle amendment of macrocyclic skeleton by the insertion of carbocyclic moiety in general and arene unit in particular, causes substantial modifications in the fundamental properties of calixphyrins. [6] For example, the presence of arene unit inside the macrocyclic core promotes the stabilization of organo-metallic complexes. [7] The m-arene ring incorporated calixbenziphyrin (2) was reported by the Latos-Grażyński group, [8] whereas the sensing experiments of the related macrocycles were accomplished by Hung and coworkers and observed selective binding with Zn(II) metal ion.…”

Section: Introductionmentioning

confidence: 99%

The (o‐p‐o)‐Terphenyl Embedded Calix[2]phyrin(2.2.1.1.1) and Its Cu(II) Complex

Pradhan,

Prasad,

Das

et al. 2024

Chemistry An Asian Journal

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The introduction of a higher arene unit as a structural motif is unprecedented in calixphyrin chemistry. Herein, the syntheses, spectral and structural characterization of heretofore anonymous terphenylene unit (o‐p‐o) incorporated calixphyrin with fused sp2meso carbons is reported. The explicitly tailored macrocyclic core is utilized to stabilize the Cu(II) metal ion. The molecular structures of the calixbenziphyrin and Cu(II) complex are unambiguously confirmed by single‐crystal X‐ray analysis. Moreover, theoretical supports uphold experimental conclusions.

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3-D Cryptand Like Normal and Doubly N-Confused Calixbenzophyrins: Synthesis and Structural Studies

Cited by 3 publications

References 34 publications

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

Creation from Confusion and Fusion in the Porphyrin World─The Last Three Decades of N-Confused Porphyrinoid Chemistry

Pyrrole‐Based Cryptand‐Like Cages: A Critical Overview of Synthetic Strategies and Applications

The (o‐p‐o)‐Terphenyl Embedded Calix[2]phyrin(2.2.1.1.1) and Its Cu(II) Complex

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