Modulation of Dual Electronic Circuits of [26]Hexaphyrins Using Internal Aromatic Straps

Mori, Haruo; Lim, Jong Min; Kim, Dongho; Osuka, Atsuhiro

doi:10.1002/ange.201308545

Cited by 16 publications

(1 citation statement)

References 29 publications

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“…5,10,15,20‐Tetrakis(2,6‐dichlorophenyl)‐21‐thiaporphyrin ( S1 ) and 2,5‐thienylene‐strapped tetrakis(2,6‐dichlorophenyl)‐[26]hexaphyrin ( S2 ) were synthesized following the methods reported in the literature from the condensation of different stochiometric of tripyrromethane and thiophene diol in the presence of Lewis acid following with oxidation reaction by 2,3‐dichloro‐5,6‐dicyano‐ p ‐benzoquinone [23,24] . The isolated pure compounds from column chromatography were character by various spectroscopic methods such as NMR, ESI‐MS, IR, and UV–vis [25,26] …”

Section: Resultsmentioning

confidence: 99%

2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg²⁺, Cu²⁺, and F⁻ Ions

Kerayu,

Hung,

Vardhaman

et al. 2024

Chemistry & Biodiversity

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The sensing behavior of 2,5‐thienylene‐bridged tetrakis(2,6‐dichlorophenyl)‐[26]hexaphyrin (2) towards various metal ions and anions were investigated by UV–vis and fluorescence spectroscopies. The molecular sensor using this strapped hexaphyrin (2) displayed highly selective and sensitive colorimetric responses to Cu2+ and Hg2+ in MeOH/THF. The spectral changes are distinctive enough in the visible region of the spectrum to enable naked‐eye detection. The detection limits of Cu2+ and Hg2+ using this chemo‐sensor in a mixed MeOH/THF solution were 1.978 and 1.283 µM, respectively, and 1.052 µM for F‐ in dichloromethane. Chemosensor 2,5‐thienylene strapped [26]hexaphyrin (2) shows absorption responses both a 1:1 molecular ratio for 2 interacting with Cu2+ and Hg2+ and a 1:2 ratio between 2 and F‐ ions.

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Section: Resultsmentioning

confidence: 99%

2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg²⁺, Cu²⁺, and F⁻ Ions

Kerayu,

Hung,

Vardhaman

et al. 2024

Chemistry & Biodiversity

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π‐Extended “Earring” Porphyrins with Multiple Cavities and Near‐Infrared Absorption

et al. 2016

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b,b-tripyrrin-bridged earring porphyrins were synthesized through Suzuki-Miyaura cross coupling reactions. These porphyrinoids have multiple cavities and can accommodate two or three metal ions per molecule.The structures of the porphyrins have been elucidated by x-ray diffraction analysis,and feature curved p planes.The electronic spectra of the porphyrins exhibit near-infrared (NIR) absorptions and metal insertion leads to red-shifted and intensified absorption features.E lectrochemical analysis and transient absorption measurements indicated that the porphyrins exhibit effective electronic communication between their central and peripheral moieties.

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Internally 2,5‐Thienylene‐Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of Möbius Aromatic Thia[28]hexaphyrins and Strong Hückel Aromaticity of its Protonated Form

et al. 2017

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Internally 1,3-phenylene-and 2,5-thienylenebridged [46]decaphyrins 2 and 3 have been synthesized. While 2 shows modest aromatic character derived from the global 46p-conjugated circuit, 3 displays larger aromatic character owingt ot he contribution of an (annuleno)annulene-type network consisting of two twisted Mçbius aromatic thia [28]hexaphyrin segments in addition to the global 46pnetwork. Upon protonation, these [46]decaphyrins underwent large structural changes to acquire strong aromaticity.Protonated 3 has been revealed to take on ap lanar structure composed of fused two triangular thia[28]hexaphyrin segments.Scheme 1. The structures of decaphyrins and their precursors.Supportinginformation and the ORCID identification number(s) for the author(s) of this article can be found under: http://dx.

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Modulation of Dual Electronic Circuits of [26]Hexaphyrins Using Internal Aromatic Straps

Cited by 16 publications

References 29 publications

2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg²⁺, Cu²⁺, and F⁻ Ions

2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg²⁺, Cu²⁺, and F⁻ Ions

π‐Extended “Earring” Porphyrins with Multiple Cavities and Near‐Infrared Absorption

Internally 2,5‐Thienylene‐Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of Möbius Aromatic Thia[28]hexaphyrins and Strong Hückel Aromaticity of its Protonated Form

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Modulation of Dual Electronic Circuits of [26]Hexaphyrins Using Internal Aromatic Straps

Cited by 16 publications

References 29 publications

2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg2+, Cu2+, and F− Ions

2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg2+, Cu2+, and F− Ions

π‐Extended “Earring” Porphyrins with Multiple Cavities and Near‐Infrared Absorption

Internally 2,5‐Thienylene‐Bridged [46]Decaphyrin: (Annuleno)annulene Network Consisting of Möbius Aromatic Thia[28]hexaphyrins and Strong Hückel Aromaticity of its Protonated Form

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2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg²⁺, Cu²⁺, and F⁻ Ions

2,5‐Thienylene‐Strapped [26]Hexaphyrin as Multifunctional Chemosensor for Hg²⁺, Cu²⁺, and F⁻ Ions