Solid‐State Photodimerization of Azaanthracene Derivative Based on a [4+4] Cycloaddition

Wang, Ruizhi; Liu, Hui; Li, Jiaofu; Tian, Jiayuan; Li, Zhibo; Zhao, Yingjie

doi:10.1002/ajoc.201800129

Asian J Org Chem

2018

DOI: 10.1002/ajoc.201800129

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Solid‐State Photodimerization of Azaanthracene Derivative Based on a [4+4] Cycloaddition

Ruizhi Wang

Hui Liu

Jiaofu Li

et al.

Abstract: Aw ater-soluble photoactive azaanthracene derivative was synthesized.I ts structure was determined by single-crystal XRD analysis. Then, [4+ +4] photodimerizations were studied both in solution and in the solid state. Owing to the suitable preorganization of the monomers, solid-state photodimerization was realized in quantitative yield with high selectivity.

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Cited by 9 publications

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Solid‐State [4+4] Cycloaddition and Cycloreversion with Use of Unpaired Hydrogen‐Bond Donors to Achieve Solvatomorphism and Stabilization

George,

Hutchins

2023

Chemistry A European J

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The crystal structure of a commercially available anthracene derivative, anthracene‐9‐thiocarboxamide, is reported here for the first time. The compound undergoes a [4+4] cycloaddition in the solid state to afford facile synthesis of the cycloadduct (CA). The cycloaddition is also reversible in the solid state using heat or mechanical force. Due to the presence of unpaired, strong hydrogen‐bond donor atoms on the CA, significant solvatomorphism is achieved, and components of the solvatomorphs self‐assemble into four different classes of supramolecular structures. The CA readily crystallizes with a variety of structurally‐diverse solvents including those containing oxygen‐, nitrogen‐, or pi‐acceptors. Some of the solvents the CA crystallized with include thiophene, benzene, and the three xylene isomers; thus, the CA was employed in industrially‐relevant solvent separation. However, in competition studies, the CA did not exhibit selectivity. Lastly, it is demonstrated that the CA crystallizes with vinyl‐containing monomers and is currently the only compound that crystallizes with both widely used monomers 4‐vinylpyridine and styrene. Solid‐state complexation of the CA with the monomers affords over a 50 °C increase in the monomer's thermal stabilities. The strategy of designing molecules with unused donors can be applied to achieve separations or volatile liquid stabilization.

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Solid‐State [4+4] Cycloaddition and Cycloreversion with Use of Unpaired Hydrogen‐Bond Donors to Achieve Solvatomorphism and Stabilization

George,

Hutchins

2023

Chemistry A European J

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show abstract

Interplay of thermochemistry and Structural Chemistry, the journal (volume 29, 2018, issues 3–4) and the discipline

2019

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Photodimerization of azaanthracene derivatives mediated by cucurbit[10]uril

Liu

et al. 2022

Chinese Chemical Letters

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Solid‐State Photodimerization of Azaanthracene Derivative Based on a [4+4] Cycloaddition

Cited by 9 publications

References 53 publications

Solid‐State [4+4] Cycloaddition and Cycloreversion with Use of Unpaired Hydrogen‐Bond Donors to Achieve Solvatomorphism and Stabilization

Solid‐State [4+4] Cycloaddition and Cycloreversion with Use of Unpaired Hydrogen‐Bond Donors to Achieve Solvatomorphism and Stabilization

Interplay of thermochemistry and Structural Chemistry, the journal (volume 29, 2018, issues 3–4) and the discipline

Photodimerization of azaanthracene derivatives mediated by cucurbit[10]uril

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