Issue 12, 2016

Effects of substitution position on crystal packing, polymorphism and crystallization-induced emission of (9-anthryl)vinylstyrylbenzene isomers

Abstract

Three (9-anthryl)vinylstyrylbenzene (ASB) position isomers were synthesized and compared. Substitution position affects temperature-induced polymorphism, crystal packing and crystallization-induced emission (CIE) properties. Different from 1,2-ASB and 1,4-ASB, 1,3-ASB undergoes a crystal-to-crystal phase transition upon heating. The crystal structure of a new phase (1,3-ASB-β) was successfully solved. Thus, the solid emission of 1,3-ASB could be tuned by polymorphism. In contrast, the solid emission of 1,4-ASB is controlled by its crystallinity. In the crystal structures of 1,2-ASB and 1,3-ASB-β, the adjacent interacting anthryls are inclined to adopt an edge-to-face configuration with C–H⋯π interactions. In contrast, the adjacent anthracene rings in the 1,4-ASB crystals are parallel to each other with π⋯π interactions. Furthermore, multiple intermolecular interaction modes such as C–H⋯π and H⋯H interactions coexist in the crystal structure of 1,4-ASB, which collectively results in a closer packing. Interestingly, 1,4-ASB displays CIE behaviour. In contrast, the emission of the other two isomers is quenched in the solid state. The effect of substitution position on the photophysical properties is systematically studied.

Graphical abstract: Effects of substitution position on crystal packing, polymorphism and crystallization-induced emission of (9-anthryl)vinylstyrylbenzene isomers

Supplementary files

Article information

Article type
Paper
Submitted
08 Dec 2015
Accepted
16 Feb 2016
First published
17 Feb 2016

CrystEngComm, 2016,18, 2098-2104

Effects of substitution position on crystal packing, polymorphism and crystallization-induced emission of (9-anthryl)vinylstyrylbenzene isomers

Y. Li, X. Yang, J. Miao, Z. Zhang and G. Sun, CrystEngComm, 2016, 18, 2098 DOI: 10.1039/C5CE02406D

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements