Crystal Packing Motifs of Oligothiophenes End-Capped with N-Containing Aryls
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- 作者：Wei Yue ; HongKun Tian ; Ninghai Hu ; Yanhou Geng ; Fosong Wang
- 刊名：Crystal Growth & Design
- 出版年：2008
- 出版时间：July 2008
- 年：2008
- 卷：8
- 期：7
- 页码：2352 - 2358
- 全文大小：1549K
- 年卷期：v.8,no.7(July 2008)
- ISSN：1528-7505
文摘
Oligothiophenes (OThs) end-capped with 3-quinolyl or pyridyl with nitrogen atom at meta-, ortho- or para-position were synthesized. The single-crystal structures of the resulting molecules, i.e., o-PyTh4, m-PyTh4, p-PyTh4, QuTh2, and QuTh3, were successfully determined by single-crystal X-ray analysis. Pyridyl end-capped OThs, o-PyTh4, m-PyTh4, and p-PyTh4, adopt the different herringbone packing arrangement in crystals depending on the position of the nitrogen atom because of the presence of weak C−H···N hydrogen bonds. The p-PyTh4 molecules are linked each other along the long axis of the molecules to form the extended chains by C−H···N dimer synthon. For m-PyTh4, the C−H···N interactions two-dimensionally extend through C−H···N trimer synthon. The weak hydrogen-bonding network is much more complex in o-PyTh4 crystals because o-PyTh4 has two crystallographically independent molecules. Two-dimensional (2D) hydrogen-bonding networks arranging along the direction of diagonals in the ab plane are formed by the C−H···N trimer synthon. The crystal packing motifs of 3-quinolyl end-capped OThs are distinctly different from pyridyl end-capped ones. The QuTh2 molecules form a 2D face to face π−π slip stacking driven by the interaction of donor and acceptor segments between the neighboring molecules. For QuTh3, the weak C−H···N hydrogen bonds between the two molecules in the same layer and the CH/π weak interactions together force the molecules to form a sandwich-herringbone crystal packing motif. These results provide a new protocol to control molecular packing arrangement of conjugated oligomers.