Jump to main content
Jump to site search

Issue 8, 2018
Previous Article Next Article

Solid state [2 + 2] photocycloaddition for constructing dimers of N,N′-diacyl-1,4-dihydropyrazines based on thiourea-induced assembly

Author affiliations

Abstract

The solid state [2 + 2] photocycloaddition of N,N′-diacyl-1,4-dihydropyrazines has been investigated using thiourea as a template to preorient the reactants in the crystalline state in a manner that is beneficial for the [2 + 2] photocycloaddition. The structures of the photoadducts, syn-dimers and cage-dimers, were determined using NMR and single-crystal X-ray diffraction. According to the topochemical principles used to assess the feasibility of solid state photochemical [2 + 2] cycloaddition, topological analysis of cocrystals consisting of the N,N′-diacyl-1,4-dihydropyrazines and thiourea, as well as the syn-dimers, was performed to investigate the influence of packing modes and non-covalent interactions on their solid state photoreactivity. The results showed that the solid state [2 + 2] reactivities of both the N,N′-diacyl-1,4-dihydropyrazines assembled using thiourea and the syn-dimers were controlled by the topochemical orientation of the potentially reactive double bonds and the H-bonding interactions within the adjacent reactive molecules.

Graphical abstract: Solid state [2 + 2] photocycloaddition for constructing dimers of N,N′-diacyl-1,4-dihydropyrazines based on thiourea-induced assembly

Back to tab navigation

Supplementary files

Publication details

The article was received on 18 Nov 2017, accepted on 24 Jan 2018 and first published on 25 Jan 2018


Article type: Paper
DOI: 10.1039/C7CE01996C
Citation: CrystEngComm, 2018,20, 1151-1157
  •   Request permissions

    Solid state [2 + 2] photocycloaddition for constructing dimers of N,N′-diacyl-1,4-dihydropyrazines based on thiourea-induced assembly

    Q. Fan, X. Duan and H. Yan, CrystEngComm, 2018, 20, 1151
    DOI: 10.1039/C7CE01996C

Search articles by author

Spotlight

Advertisements