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Issue 33, 2008
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Self-assembly of highly luminescent bi-1,3,4-oxadiazole derivatives through electron donor–acceptor interactions in three-dimensional crystals, two-dimensional layers and mesophases

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Abstract

We report on the synthesis and self-assembly of a new series of highly luminescent bi-1,3,4-oxadiazole derivatives [2,2′-bis(4-alkoyphenyl)-bi-1,3,4-oxadiazole, BOXD-n, n = 1, 3, 4, 5, 6, 7, 10, 16]. Fully conjugated conformations were demonstrated either by computer simulation or in a single-crystal state. Well-defined 3D donor–acceptor (DA) architectures with strong face-to-face and edge-to-edge donor–acceptor interactions were observed in the single-crystal structure of BOXD-1. Highly oriented face-on two-dimensional DA layered structures due to edge-to-edge donor–acceptor interactions were observed on highly oriented pyrolytic graphite (HOPG) in BOXD-7 and BOXD-16. Nematic phase, smectic C phase with large tilted angle (θ ≈ 50°) and relatively large transition enthalpic values and a highly ordered smectic X phase were demonstrated in BOXD-n (n = 5, 6, 7, 8, 10, 16) through tailing the terminal chains and relatively large scale monodomains were prepared in the smectic X phase of BOXD-5 even without any surface treatment. Strong blue fluorescent emissions were observed in BOXD-6 either in cyclohexane (ФF ≈ 92%) or in solid state (ФF ≈ 57%). The donor–acceptor interactions between alkyoxyphenylene rings and 1,3,4-oxadiazole rings were thought to be the driving force for the molecules to self-assemble into a large angle tilted layered structure.

Graphical abstract: Self-assembly of highly luminescent bi-1,3,4-oxadiazole derivatives through electron donor–acceptor interactions in three-dimensional crystals, two-dimensional layers and mesophases

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Supplementary files

Article information


Submitted
11 Mar 2008
Accepted
03 Jun 2008
First published
09 Jul 2008

J. Mater. Chem., 2008,18, 3954-3964
Article type
Paper

Self-assembly of highly luminescent bi-1,3,4-oxadiazole derivatives through electron donor–acceptor interactions in three-dimensional crystals, two-dimensional layers and mesophases

S. Qu, X. Chen, X. Shao, F. Li, H. Zhang, H. Wang, P. Zhang, Z. Yu, K. Wu, Y. Wang and M. Li, J. Mater. Chem., 2008, 18, 3954
DOI: 10.1039/B804189J

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