Abstract
Two 9,10-distyrylanthracene (DSA) derivatives CNDSA and t-BUDSA were designed and synthesized, and their photophysical properties and crystal structures were investigated. Compared to DSA, the maximum emission peaks of the two compounds showed red-shift not only in THF solution, but also in crystals, because the introduction of electron-withdrawing substituents to DSA leads to more dispersion of the electrons in the molecules. The two crystals of CNDSA and t-BUDSA show strong fluorescence with the efficiency Φ F of 45% and 33%, respectively, which may be resulted from no obvious π-π interactions between molecules inside the crystal due to the large distance between the two adjacent molecules and nearly no overlap between the central anthracene planes. The analysis of crystal structures of the two compounds indicated that the molecules are arranged in the same conformation and orientation in their crystals, i.e. uniaxially oriented packing crystal, because of the supramolecular interaction of CH/π in the two crystals and additional C-H…N interactions in CNDSA.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Yanagi H, Ohara T, Morikawa T. Self-waveguided gain-narrowing of blue light emission from epitaxially oriented p-sexiphenyl crystals. Adv Mater, 2001, 13: 1452–1455
Tok J B H, Bao Z A. Recent advances in flexible and stretchable electronics, sensors and power sources. Sci China-Chem, 2012, 55: 718–725
Wang J H, Liu L, Liu G F, et al. Three novel photoisomeric compounds of the 4-acyl pyrazolone derivants: Crystal structures and substituent effects on photo-isomerism in solid state. Sci China Ser B-Chem, 2008, 51: 661–668
Li Y P, Shen F Z, Wang H, et al. Supramolecular network conducting the formation of uniaxially oriented molecular crystal of cyano substituted oligo(p-phenylenevinylene) and its amplified spontaneous emission (ASE) behavior. Chem Mater, 2008, 20: 7312–7318
Cáceres D, Cebrián C, Rodríguez A M, et al. Optical waveguides from 4-aryl-4H-1,2,4-triazole-based supramolecular structures. Chem Commun, 2013, 49: 621–623
Park S, Kwon O H, Kim S, et al. Imidazole-based excited-state intramolecular proton-transfermaterials: Synthesis and amplified spontaneous emission from a large single crystal. J Am Chem Soc, 2005, 127: 10070–10074
Yanagi H, Yoshiki A. Stimulated resonance Raman scattering from epitaxially oriented crystals of biphenyl-capped thiophene. Appl Phys Lett, 2004, 84: 4783–4785
Varghese S, Yoon S J, Calzado E M, et al. Stimulated resonance Raman scattering and laser oscillation in highly emissive distyrylbenzene-based molecular crystals. Adv Mater, 2012, 24: 6473–6478
Koren A B, Curtis M D, Francis A H, et al. Intermolecular interactions in π-stacked conjugated molecules. Synthesis, structure, and spectral characterization of alkyl bithiazole oligomers. J Am Chem Soc, 2003, 125: 5040–5050
Yan X H, Su Y, Li J B, et al. Uniaxially oriented peptide crystals for active optical waveguiding. Angew Chem Int Ed, 2011, 50: 11186–11191
Xu B, He J T, Dong Y J. Aggregation emission properties and self-assembly of conjugated oligocarbazoles. Chem Commun, 2011, 47: 6602–6604
Gierschner J, Ehni M, Egelhaaf H J, et al. Solid-state optical properties of linear polyconjugated molecules: π-stack contra herringbone. J Chem Phys, 2005, 123: 144914–144922
Xu B, Fang H H, Dong Y J, et al. Solid state emission enhancement of 9,10-distyrylanthracene derivatives and amplified spontaneous emission from a large single crystal. New J Chem, 2010, 34: 1838–1842
Qin A J, Zhang Y, Han N, et al. Preparation and self-assembly of amphiphilic polymer with aggregation-induced emission characteristics. Sci China-Chem, 2012, 55: 772–778
Xue Y N, Chai S Y, Bie G J, et al. Synthesis and properties of a novel aggregation-induced emitter 9,10-bis[2-(1-methyl-1H-pyrrol-2-yl) vinyl]anthracene (in Chinese). Acta Chim Sinica, 2008, 66: 1577–1582
He J T, Xu B, Chen F P, et al. Aggregation-induced emission in the crystals of 9,10-distyryl anthracene derivatives: The essential role of restricted intramolecular torsion. J Phys Chem C, 2009, 113: 9892–9899
Dong Y J, Xu B, Zhang J B, et al. Supramolecular interactions induced fluorescent organic nanowires with high quantum yield based on 9,10-distyrylanthracene. Cryst Eng Comm, 2012, 14: 6593–6598
Dong Y J, Xu B, Zhang J B, et al. Piezochromic luminescence based on the molecular aggregation of 9,10-bis((E)-2-(pyrid-2-yl)vinyl) anthracene. Angew Chem Int Ed, 2012, 51: 10782–10785
Dong Y J. Small molecules based on divinylanthracene: Design and synthesis, crystal structure, self-assembly and piezochromic properties (in Chinese). Dissertation for Master Degree. Changchun: Jilin University, 2012
Wang L J, Xu B, Zhang J B, et al. Theoretical investigation of electronic structure and charge transport property of 9, 10-distyrylan-thracene (DSA) derivatives with high solid-state luminescent efficiency. Phys Chem Chem Phys, 2013, 15: 2449–2458
Jenning W B, Farrell B M, Malone J F. Attractive intramolecularedge-to-face aromatic interactions in flexible organic molecules. Acc Chem Res, 2001, 34: 885–894
Weiss H C, Bläser D, Boese R, et al. C-H…π interactions in ethynylbenzenes: The crystal structures of ethynylbenzene and 1,3,5-triethynylbenzene, and a redetermination of the structure of 1,4-diethynylbenzene. Ch Chem Commun, 1997, 1703–17
Steiner T. The hydrogen bond in the solid state. Angew Chem Int Ed, 2002, 41: 48–76
Taylor R, Kennard O. Crystallographic evidence for the existence of C-H-O, C-H-N, and C-H-Cl hydrogen bonds. J Am Chem Soc, 1982, 104: 5063–5070
Author information
Authors and Affiliations
Corresponding authors
Additional information
This article is published with open access at Springerlink.com
Rights and permissions
This article is published under an open access license. Please check the 'Copyright Information' section either on this page or in the PDF for details of this license and what re-use is permitted. If your intended use exceeds what is permitted by the license or if you are unable to locate the licence and re-use information, please contact the Rights and Permissions team.
About this article
Cite this article
Chen, J., Ma, S., Xu, B. et al. Molecular crystals based on 9,10-distyrylanthracene derivatives with high solid state fluorescence efficiency and uniaxial orientation induced by supramolecular interactions. Chin. Sci. Bull. 58, 2747–2752 (2013). https://doi.org/10.1007/s11434-013-5897-9
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11434-013-5897-9