Article ID Journal Published Year Pages File Type
1402195 Journal of Molecular Structure 2015 9 Pages PDF
Abstract

•Six novel macrocyclic and chain co-crystals 1–6 were generated.•The “clip-like” resorcinol acts as H-bonding donor and template in 1–3.•They display interesting solid-state luminescent properties.•They are blue-shifted 55–60 nm with decreased emission intensities.•Their luminescence is related to H-bonds, conformations, arranging dispositions.

Based on 2,6-bis((pyridin-4-yl)methylene)cyclohexanone (A) and N-methyl-3,5-bis((pyridin-4-yl)methylene)-4-piperidone (B) with coformers, three novel macrocyclic co-crystals, (A)⋅(resorcinol) (1), (A)⋅(1,3,5-benzenetriol) (2), (B)2⋅(1,3,5-benzenetriol)2 (3) and three chain co-crystals, (A)⋅(hydroquinone) (4), (A)⋅(isophthalic acid) (5), (B)⋅(isophthalic acid) (6) have been synthesized and structurally characterized by IR, 1H NMR and X-ray crystal structure analysis. Structural analysis indicates that four-component macrocycles in 1–3 are generated from “clip-like” resorcinol templates and building blocks, while 4–6 show infinite H-bonding chains. In addition, the luminescent properties of A, B and 1–6 are investigated primarily in the solid state. Compared with free building blocks, 1–6 are blue-shifted 55–60 nm with decreasing emission intensities in spite of the enhancement in 6. The change of luminescent properties might be caused mainly by incorporation of coformers into co-crystals, including H-bonds, molecular conformations, arranging dispositions and π–π characteristics. It might have potential applications for crystal engineering to construct patentable crystals with interesting luminescent properties.

Related Topics
Physical Sciences and Engineering Chemistry Organic Chemistry
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