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Molecular crystals based on 9,10-distyrylanthracene derivatives with high solid state fluorescence efficiency and uniaxial orientation induced by supramolecular interactions

Molecular crystals based on 9,10-distyrylanthracene derivatives with high solid state fluorescence efficiency and uniaxial orientation induced by supramolecular interactions
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摘要 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 fluores- cence with the efficiency F of 45% and 33%, respectively, which may be resulted from no obvious-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 interac- tion of CH/ in the two crystals and additional C-H···N interactions in CNDSA. 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 fluores- cence with the efficiency t/~ of 45% and 33%, respectively, which may be resulted from no obvious re-re interactions between molecules inside the crystal due to the large distance between the two adjacent molecules and nearly no overlap between the cen- tral 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 interac- tion of CH/~ in the two crystals and additional C-H'-'N interactions in CNDSA.
出处 《Chinese Science Bulletin》 SCIE EI CAS 2013年第22期2747-2752,共6页
基金 supported by the National Basic Research Program of China(2013CB834702) the National Natural Science Foundation of China(21074045,21204027,21221063) the Research Fund for the Doctoral Program of Higher Education of China the Project of Jilin Province(20100704)
关键词 超分子相互作用 分子晶体 晶体取向 荧光效率 衍生物 单轴 吸电子取代基 晶体结构分析 9,10-distyrylanthracene derivatives, high solid state fluorescence efficiency, uniaxially oriented packing
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