Uncovering tetrazoles as building blocks for constructing discrete and polymeric assemblies

Dey, Soumya; Aggarwal, Medha; Chakraborty, Debsena; Mukherjee, Partha Sarathi

doi:10.1039/d4cc01616e

Chem. Commun.

2024

DOI: 10.1039/d4cc01616e

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Uncovering tetrazoles as building blocks for constructing discrete and polymeric assemblies

Soumya Dey,

Medha Aggarwal,

Debsena Chakraborty

et al.

Abstract: Metal-organic self-assembly with flexible moieties is a budding field of research due to the possibility of the formation of unique architectures. Tetrazole, characterised by four nitrogen atoms in a five-member...

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2024

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Cited by 3 publications

References 117 publications

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Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Aggarwal,

Banerjee,

Hickey

et al. 2024

Angewandte Chemie

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The dynamic behaviour of metal‐ligand bonding cultivates stimuli‐mediated structural transformations in self‐assembled molecular architectures. The propensity of synthetically designed self‐assembled systems to interchange between higher‐order architectures is increased multi‐fold when the building blocks have higher conformational degrees of freedom. Herein, we report a new ligand, (2,7‐bis(di(pyridin‐4‐yl)amino)‐9H‐fluoren‐9‐one) (L), which, upon self‐assembly with a cis‐[(ethylene‐1,2‐diamine)Pd(NO3)2] acceptor (M), resulted in the formation of a M6L3 trifacial barrel (C1) in water. Interestingly, during crystallization, a rare M12L6 triangular orthobicupola architecture (C2) was generated along with C1. C2 could also be generated in solution via the application of several stimuli. C1 in aqueous medium could stabilize one trans‐stilbene (tS) or cis‐stilbene (cS) molecule in its cavity, with a selectivity for the former from their mixture. Moreover, C1 acted as an effective host to prevent the otherwise facile photoisomerization of tS to cS inside its hydrophobic cavity under UV irradiation. Conversely, the visible‐light‐induced reverse isomerization of encapsulated cS to encapsulated tS could be achieved readily due to the better stabilization of tS within the cavity of C1 and its transparency to visible light. A multi‐functional system was therefore designed, which at the same time is stimuli‐responsive, shows isomer selectivity, and photo‐protects trans‐stilbene.

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Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Aggarwal,

Banerjee,

Hickey

et al. 2024

Angewandte Chemie

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Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Aggarwal,

Banerjee,

Hickey

et al. 2024

Angew Chem Int Ed

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Facile N‐Modification of NH‐Tetrazoles via Rh(II)‐Catalyzed N−H Insertion Involving Structurally Diverse Diazo Reagents

Radiupov,

Kantin,

Dar'in

2024

Eur J Org Chem

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A convenient method for the N‐modification of NH‐tetrazoles by the Rh(II)‐catalyzed insertion reaction of diazocarbonyl compounds into the N‐H bond has been proposed. A wide range of structurally diverse diazo reagents (including heterocyclic ones) as well as tetrazoles with different substituents in the fifth position can be used to prepare 2,5‐disubstituted tetrazole derivatives in good and high yields and with high regioselectivity. It is shown that the regioselectivity of the reaction can decrease in the presence of electron withdrawing groups in the tetrazole, as well as in the presence of proton acids.

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Uncovering tetrazoles as building blocks for constructing discrete and polymeric assemblies

Abstract: Metal-organic self-assembly with flexible moieties is a budding field of research due to the possibility of the formation of unique architectures. Tetrazole, characterised by four nitrogen atoms in a five-member...

Cited by 3 publications

References 117 publications

Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Facile N‐Modification of NH‐Tetrazoles via Rh(II)‐Catalyzed N−H Insertion Involving Structurally Diverse Diazo Reagents

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Uncovering tetrazoles as building blocks for constructing discrete and polymeric assemblies

Abstract: Metal-organic self-assembly with flexible moieties is a budding field of research due to the possibility of the formation of unique architectures. Tetrazole, characterised by four nitrogen atoms in a five-member...

Cited by 3 publications

References 117 publications

Stimuli‐Mediated Structural Interchange Between Pd6 and Pd12 Architectures: Selective Recognition of E‐Stilbene by the Pd6 Architecture and its Photoprotection

Stimuli‐Mediated Structural Interchange Between Pd6 and Pd12 Architectures: Selective Recognition of E‐Stilbene by the Pd6 Architecture and its Photoprotection

Stimuli‐Mediated Structural Interchange Between Pd6 and Pd12 Architectures: Selective Recognition of E‐Stilbene by the Pd6 Architecture and its Photoprotection

Facile N‐Modification of NH‐Tetrazoles via Rh(II)‐Catalyzed N−H Insertion Involving Structurally Diverse Diazo Reagents

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Product

Resources

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Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection

Stimuli‐Mediated Structural Interchange Between Pd₆ and Pd₁₂ Architectures: Selective Recognition of E‐Stilbene by the Pd₆ Architecture and its Photoprotection