Quinoxaline-fused octaphyrin(2.0.0.0.2.0.0.0). A rudimentary chemosensor

Tan, Bingbin; Ding, Wenjing; Yin, Yilong; Xu, Kui; Yin, Ying; Chen, Xi; Huang, Zhengxi; Wu, Lihong; Sessler, Jonathan L.; Zhang, Zhan

doi:10.1039/d2cc05604f

Cited by 2 publications

(3 citation statements)

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“…This ruled out the possibility of deprotonation and substantiated the scope for anion sensing via hydrogen bonding (Figure S6–6). Thus, H21 can serve as a simple colorimetric sensor for F − and OH − ions which can be enlisted into few porphyrinoid based colorimetric sensors known for hydroxide ions [17,18,30] …”

Section: Resultsmentioning

confidence: 99%

“…Thus, H21 can serve as a simple colorimetric sensor for F À and OH À ions which can be enlisted into few porphyrinoid based colorimetric sensors known for hydroxide ions. [17,18,30]…”

Section: Anion Sensing Studiesmentioning

confidence: 99%

“…Cyclic and acyclic ligands with multiple donor sites have been flourishing in the past decade, especially in the field of fluoride recognition and transport. [13][14][15][16] Quite recently, Zhang and coworkers had reported quinoxaline-fused porphycene [17] and octaphyrin C [18] that acts as a rudimentary sensor for F À and OH À , operating via deprotonation mechanism. Although the figure of eight conformation of C was expected to disfavour guest binding, the exposed pyrrolic NH groups enabled colorimetric sensing of various solvents as well as basic anions.…”

Section: Introductionmentioning

confidence: 99%

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Template Assisted Formation of 32 and 34π Octaphyrins Embedded with Dithienopyrrole Cores: A New Scaffold to Unravel Proton Coupled Redox Switching and (Anti)Aromaticity

Edwin,

Krishnan,

Jayaprakash

et al. 2024

Chemistry A European J

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Herein, we report two distinct octaphyrins obtained by the condensation of new dithieno[3,2‐b:2',3'‐d]pyrrole based tetrapyrrane under two different acidic conditions. Fourfold meso‐substituted octaphyrin was the major product when the reaction was performed in the presence of an aryl aldehyde using trifluoroacetic acid. Whereas, the sixfold meso‐substituted octaphyrin was obtained when the precursor was condensed with pentafluorobenzaldehyde using para‐toluenesulfonic acid. Such a template effect of aryl aldehydes in oxidative coupling reactions is realized for the first time in literature. Experimental and theoretical studies suggested that the oxidized form of fourfold meso‐substituted octaphyrin is 32p antiaromatic and undergoes proton‐coupled electron transfer (PCET) to the protonated form of 34p aromatic congener upon treatment with protic acids. Furthermore, small organic molecules such as alcohols and amines were also found to promote chemical reduction. Single crystal X‐ray structure revealed that the aromatic counterpart is highly planar and stabilized by several intermolecular H‐bonding and F‐F interactions, leading to a large 3D supramolecular arrangement and exhibited colorimetric sensing for fluoride and hydroxide anions. On the other hand, sixfold meso‐substituted octaphyrin did not show (anti)aromatic features, PCET or anion sensing, but its intriguing absorption features associated with protonation could make it an ideal candidate for pH‐dependent bioimaging.

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Section: Resultsmentioning

confidence: 99%

“…Thus, H21 can serve as a simple colorimetric sensor for F À and OH À ions which can be enlisted into few porphyrinoid based colorimetric sensors known for hydroxide ions. [17,18,30]…”

Section: Anion Sensing Studiesmentioning

confidence: 99%