Cyclo[<i>n</i>]carbons and catenanes from different perspectives: disentangling the molecular thread

Kozáková, Silvia; Alharzali, Nissrin; Černušák, Ivan

doi:10.1039/d3cp03887d

Phys. Chem. Chem. Phys.

2023

DOI: 10.1039/d3cp03887d

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Cyclo[n]carbons and catenanes from different perspectives: disentangling the molecular thread

Silvia Kozáková,

Nissrin Alharzali,

Ivan Černušák

Abstract: All-carbon atomic rings, cyclo[n]carbons, have recently attracted vivid attention of experimentalists and theoreticians. Among them, cyclo[18]carbon is the most studied system. In this paper, we summarize and review various properties...

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Cited by 4 publications

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Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu₂C(CH₂PPh₂)₂)Pt((C≡C)_nSiEt₃)₂ (n=2, 3) and Macrocycles Comprised of Four L₂Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

Collins,

Gladysz

2024

Chemistry A European J

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The overarching goal of this study is to effect the elimination of platinum from adducts with cis –C≡C−Pt−C≡C‐ linkages, thereby generating novel conjugated polyynes. Thus, the bis(hexatriynyl) complex trans‐(p‐tol3P)2Pt((C≡C)3H)2 is treated with 1,3‐diphosphines R2C(CH2PPh2)2 to generate (R2C(CH2PPh2)2)2Pt((C≡C)3H)2 (14; R=c, n‐Bu; e, p‐tolCH2). These condense with the diiodide complexes R2C(CH2PPh2)2PtI2 (9 a,c) in the presence of CuI (cat.) and excess HNEt2 to give the title macrocycles [(R2C(CH2PPh2)2)Pt(C≡C)3]4 (16 c,e) as adducts of the byproduct [H2NEt2]+ I− (30–66 %). DOSY NMR experiments establish that this association is maintained in solution, but NaOAc removes the ammonium salt. The bis(triethylsilylpolyynyl) complexes (n‐Bu2C(CH2PPh2)2)Pt((C≡C)nSiEt3)2 (n=2, 3) are synthesized analogously to 14 c. They react with I2 at rt to give mainly the diiodide complex 9 c and the coupling product Et3Si(C≡CC≡C)nSiEt3. The possibility of competing reactions giving IC≡C species is investigated. Analogous reactions of the Pt4C24 macrocycle 16 c also give 9 c, but no sp 13C NMR signals or mass spectrometric Cxz+ ions (x=24–100) could be detected. It is proposed that some cyclo[24]carbon is generated, but then rapidly converts to other forms of elemental carbon. No cyclotetracosane (C24H48) is detected when this sequence is carried out in the presence of PtO2 and H2.

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Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu₂C(CH₂PPh₂)₂)Pt((C≡C)_nSiEt₃)₂ (n=2, 3) and Macrocycles Comprised of Four L₂Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

Collins,

Gladysz

2024

Chemistry A European J

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On the supramolecular interactions into a pH‐ and Metal‐Actuated Molecular Shuttle: some insights from QTAIM modeling

Zazza,

Sanna,

Borocci

et al. 2024

ChemPhysChem

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Supramolecular contacts responsible for chemical interaction of cucurbit[7]uril (CB[7]) macrocycle on a Tolyl‐Viologen‐Phenylene‐Imidazole (T‐VPI) molecular thread, at acid pH (T‐VPI‐H+) or after Ag+ cation addition (T‐VPI‐Ag+), are analytically addressed in a computational framework combining Quantum Theory of Atoms in Molecules (QTAIM) with Density Functional Theory (DFT). In this respect, the crystallographic structure (CCDC number 2217466) is taken as reference condition for addressing the nature of the chemical interactions driving the shuttling of the CB[7] between T and P stations recently observed in dilute water solutions. Beside the host(CB[7]) vs guest(T‐VPI‐H+ or T‐VPI‐Ag+) complexation, the coordination sphere of the Ag+ cation is also investigated by means of local electronic energy density ‐ H(r) ‐ descriptors. The derived non‐covalent interaction patterns are found to support diagnostic 1H NMR signals used for detecting the mutual position of the CB[7] along the axle. This work highlights the potentialities of a QTAIM based approach in the characterization of supramolecular and metal‐complexation effects in molecular aggregates such as not‐interlocked synthetic molecular shuttles.

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Chemistry of Cyclo[18]Carbon (C₁₈): A Review

Pooja,

Yadav,

Pawar

2024

The Chemical Record

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Carbon‐based allotropes are propelling a technological revolution in communication, sensing, and computing, concurrently challenging fundamental theories of the previous century. Nevertheless, the demand for advanced carbon‐based materials remains substantial. The crux lies in the efficient and reliable engineering of novel carbon allotrope. Although C18 has undergone theoretical and experimental investigation for an extended period, its preparation and direct observation in the condensed phase occurred only recently through STM/AFM techniques. The distinctive cyclic ring structure and the dual 18‐center π delocalization character introduce various uncommon properties to C18, rendering it a subject worthy of in‐depth exploration. In this context, this review delves into past developments contributing to the state‐of‐the‐art understanding of C18 and provides insights into how future endeavours can expedite practical applications. Encompassing a broad spectrum, this review comprehensively investigates almost all facets of C18, including geometric characteristics, electron delocalization, bonding nature, aromaticity, reactivity, electronic excitation, UV/Vis spectrum, intermolecular interaction, response to external fields, electron affinity, ionization, and other molecular properties. Moreover, the review also outlines representative strategies for the direct synthesis and characterization of C18 using atom manipulation techniques. Following this, C18‐based complexes are summarized, and potential applications in catalysis, electrochemical devices, optoelectronics, and sensing are discussed.

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Cyclo[n]carbons and catenanes from different perspectives: disentangling the molecular thread

Abstract: All-carbon atomic rings, cyclo[n]carbons, have recently attracted vivid attention of experimentalists and theoreticians. Among them, cyclo[18]carbon is the most studied system. In this paper, we summarize and review various properties...

Cited by 4 publications

References 172 publications

Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu₂C(CH₂PPh₂)₂)Pt((C≡C)_nSiEt₃)₂ (n=2, 3) and Macrocycles Comprised of Four L₂Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu₂C(CH₂PPh₂)₂)Pt((C≡C)_nSiEt₃)₂ (n=2, 3) and Macrocycles Comprised of Four L₂Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

On the supramolecular interactions into a pH‐ and Metal‐Actuated Molecular Shuttle: some insights from QTAIM modeling

Chemistry of Cyclo[18]Carbon (C₁₈): A Review

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Cyclo[n]carbons and catenanes from different perspectives: disentangling the molecular thread

Abstract: All-carbon atomic rings, cyclo[n]carbons, have recently attracted vivid attention of experimentalists and theoreticians. Among them, cyclo[18]carbon is the most studied system. In this paper, we summarize and review various properties...

Cited by 4 publications

References 172 publications

Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu2C(CH2PPh2)2)Pt((C≡C)nSiEt3)2 (n=2, 3) and Macrocycles Comprised of Four L2Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu2C(CH2PPh2)2)Pt((C≡C)nSiEt3)2 (n=2, 3) and Macrocycles Comprised of Four L2Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

On the supramolecular interactions into a pH‐ and Metal‐Actuated Molecular Shuttle: some insights from QTAIM modeling

Chemistry of Cyclo[18]Carbon (C18): A Review

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Product

Resources

About

Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu₂C(CH₂PPh₂)₂)Pt((C≡C)_nSiEt₃)₂ (n=2, 3) and Macrocycles Comprised of Four L₂Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

Platinum Elimination from Bis(triethylsilylpolyynyl) Complexes (n‐Bu₂C(CH₂PPh₂)₂)Pt((C≡C)_nSiEt₃)₂ (n=2, 3) and Macrocycles Comprised of Four L₂Pt Corners and Four C≡CC≡CC≡C Linkers; An Approach to Cyclo[24]carbon

Chemistry of Cyclo[18]Carbon (C₁₈): A Review