Mehrstufige reversible Redoxsysteme, XLII. [2 + 2]‐Photocycloadditionen von α‐Styrylpyrylium‐Salzen zu 4,4′‐(1,3‐Cyclobutandiyl)bis(pyrylium)‐Salzen sowie deren thermische und baseninduzierte Cycloreversionen

Hesse, Konrad; Hünig, Siegfried

doi:10.1002/jlac.198519850408

Cited by 21 publications

(2 citation statements)

References 44 publications

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“…The light-mediated dimerization of 2,6-di( tert -butyl)styryl pyrylium salts 1 was first described by Hesse and Hünig in 1985 (Figure ). The mechanistic details of this reaction were later revealed by Novak et al on the basis of comprehensive crystallographic studies . Inspired by this, we designed monomer 3 and set out to synthesize it in a straightforward fashion.…”

Section: Resultsmentioning

confidence: 99%

A Two-Dimensional Polymer Synthesized through Topochemical [2 + 2]-Cycloaddition on the Multigram Scale

et al. 2017

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The single-crystal-to-single-crystal (scsc) synthesis of a 2D polymer based on photochemically triggered [2 + 2]-cycloaddition is reported. Both monomer and polymer single crystals are analyzed by X-ray diffraction, which is the first case of a scsc two-dimensional polymerization based on this cycloaddition and the third ever case for a scsc synthesis of a 2D polymer. The product crystals at quantitative conversion are wet-exfoliated under mild conditions and afford countless features that are single and double layers as judged by their AFM heights of h ≈ 1.2 ± 0.5 and 2.2 ± 0.5 nm, respectively. The X-ray-structure-based molecular weight of the 2D polymers and their degree of polymerization per μm are M = 360 MDa and P = 464 900, respectively. The sheet size is on the order of 5 × 5 μm.

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Section: Resultsmentioning

confidence: 99%

A Two-Dimensional Polymer Synthesized through Topochemical [2 + 2]-Cycloaddition on the Multigram Scale

et al. 2017

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“…The dimerization of the "arms" (control molecule R1) in single-crystalline state has been well identified (Figure 1b). 62,63 The single crystal of M1 could be easily obtained by recrystallization in the mixture of acetic acid and formic acid and is rather stable in the air (for detail see Supporting Information section 1.3). In the resulting crystal structure (space group R3̅ ), M1 adopted the desired C3symmetry, and the three arms were packed in a head-to-tail fashion to form hexagonal plane tiling (Figures 1d and 2a).…”

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confidence: 99%

Highly Efficient Preparation of Single-Layer Two-Dimensional Polymer Obtained from Single-Crystal to Single-Crystal Synthesis

Hao

Mücke

et al. 2021

J. Am. Chem. Soc.

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A two-dimensional polymer (2DP) single crystal (T-2DP) with submillimeter size was synthesized by single-crystal to single-crystal transformation based on photochemical [2 + 2]-cycloaddition. A successful conversion from monomer to polymer was achieved in the single-crystal state. The structure information with an atomic resolution of both the monomer and 2DP was given through single-crystal X-ray diffraction. By simply treated with trifluoroacetic acid (TFA) under mild conditions, an unprecedented efficiency of exfoliation was achieved. The triazine core in T-2DP could be protonated by TFA, which resulted in a solution-like sample with >60% of monolayers. The size of the exfoliated monolayer reaches to several hundreds of μm2. This is another precious example of 2DP single crystal with nearly perfect structure and large enough size. The successful preparation of the highly desirable 2DP “solution” for a long time containing large sized and large amount of 2DP monolayers may open up new prospects for the basic properties study and the applications of 2DPs.

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Synthesis, Structures and Topochemistry of 2-Monovinyl-Substituted 1,4-Benzoquinones

Irngartinger¹,

Stadler

1998

Eur. J. Org. Chem.

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In the course of topochemical investigations of substituted quinones the 2‐monovinyl‐substituted 1,4‐benzoquinones 1 were synthesized by electrochemical oxidation of the corresponding 1,4‐dimethoxybenzene derivatives 3 to the quinone bisketals 4 and subsequent hydrolysis. In solution, the aryl‐substituted vinylquinones 1a−1t underwent unexpected Diels‐Alder additions. The stereochemically unique course of the reaction was proved spectroscopically and by X‐ray structure analysis of the dimer 8k. As a basic requirement for the topochemical studies, the crystal structures of eight quinones 1 were determined by X‐ray diffraction. In the crystals of 1a, 1c, 1e, 1f, 1i and 1n with an α‐type packing arrangement, the vinylic double bonds have short contacts (< 4.4 Å) across a centre of symmetry. The quinone 1k crystallizes in a β arrangement with short distances (< 4.0 Å) between molecules related by translation and in a γ arrangement without suitable contacts. The crystals of all quinones 1 were irradiated with UV light to perform [2+2] cycloadditions. The photoreactive quinones dimerized exclusively at the vinylic double bonds, resulting in the corresponding cyclobutanes 9. Topochemically controlled the dimers 9a−9c, 9e, 9l−9n, 9q, 9r and 9u with molecular Ci symmetry were formed whereas the dimers 9k and 9t have Cs symmetry. The structures of the cyclobutanes were determined by spectroscopical investigations and in the case of 9b, 9e and 9r additionally by X‐ray analysis. Despite short contacts, crystals of 1f and 1i were photostable. This is probably because of insufficient lattice flexibility indicated by relatively high densities.

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Mehrstufige reversible Redoxsysteme, XLII. [2 + 2]‐Photocycloadditionen von α‐Styrylpyrylium‐Salzen zu 4,4′‐(1,3‐Cyclobutandiyl)bis(pyrylium)‐Salzen sowie deren thermische und baseninduzierte Cycloreversionen

Cited by 21 publications

References 44 publications

A Two-Dimensional Polymer Synthesized through Topochemical [2 + 2]-Cycloaddition on the Multigram Scale

A Two-Dimensional Polymer Synthesized through Topochemical [2 + 2]-Cycloaddition on the Multigram Scale

Highly Efficient Preparation of Single-Layer Two-Dimensional Polymer Obtained from Single-Crystal to Single-Crystal Synthesis

Synthesis, Structures and Topochemistry of 2-Monovinyl-Substituted 1,4-Benzoquinones

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