1,6-Diaminoperylene bisimide with a highly twisted perylene core

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• 作者：CHE-WEI CHANG ; FANG-YUN CHIEN ; JIUN-WEI HU ; HSING-YANG TSAI…
• 关键词：Perylene bisimides ; x ; ray diffraction ; axial chirality ; density functional theory.
• 刊名：Journal of Chemical Sciences
• 出版年：2017
• 出版时间：February 2017
• 年：2017
• 卷：129
• 期：2
• 页码：149-156
• 全文大小：
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry/Food Science, general;
• 出版者：Springer India
• ISSN：0973-7103
• 卷排序：129

文摘

1,6-Diaminoperylene bisimide (1) was synthesized and characterized by single-crystal X-ray diffraction. To the best of our knowledge, this is the first time that the structure of 1,6-disubstituted perylene bisimide has been reported. The crystal belongs to triclinic, space group P-1, with a = 10.3966(10), b = 15.3398(16), c = 16.8495(17) Å, α = 79.490(4)∘, β = 87.055(3)∘, γ = 79.423(3)∘, and Z = 2. Compound 1 possesses two intramolecular C–H ⋯N hydrogen bonds, which generate two S(6) ring motifs. The central perylene core of 1 is twisted with dihedral angles of 19.48(2) ∘ and 19.50(2) ∘; this twist configuration induces the axial chirality in this family of perylene bisimide chromophores. Density functional theory (DFT) calculations also show that the core twist angles of 1,6-diaminoperylene bisimide are larger than those of 1,7-diaminoperylene bisimide, which may account for the fact that the 1,7-regioisomer has a more extended effective conjugation length than the 1,6-regioisomer.