Intermolecular Interaction of [60]Fullerene with Troger's Base Analogues
Intermolecular Interaction of [60]Fullerene with Troger's Base Analogues
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[60]富勒烯与 Troger 碱类似物的分子间相互作用
DOI：
10.1080/1536383x.2013.787608
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发表时间：
2014
期刊：
影响因子：
--
通讯作者：
Tadashi Hasegawa
中科院分区：
文献类型：
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作者：
Michio Yamada;Konomi Tokutomi;Ayaka Takehara;Yusuke Sakai;Yutaka Maeda;Tadashi Hasegawa
合成了Tröger碱(Tb，1)及其类似物，并通过滴定实验评价了它们与C60的超分子络合能力。结果表明，基于荧烯的Tb类似物(2)和基于生物辛基荧基的Tb类似物(3)与C60以1：1的比例结合形成相应的络合物，而Tb1则没有。滴定实验表明，3/C60的结合常数(KASS)(48.1±7.9M−1)大于2/C60(13.7±1.4M−1)，同时也证实了1：1结合络合物2/C60和3/C60的形成。理论计算表明，2和3有合适的空穴来拥抱C60。这些结果表明，在与C60的超分子络合中，不仅荧烯基团与C60表面之间的π/π相互作用，而且辛基与C60表面之间的CH/π相互作用也是有效的。
Tröger's base (TB,1) and its analogues were synthesized and were subject to the titration experiments to evaluate their ability of supramolecular complexation with C60. Results demonstrate clearly that the fluorene-based TB analogue (2) and the bioctylfluorene-based TB analogue (3) show 1:1 binding with C60to form the corresponding complexes while TB1does not. Titration experiments exhibited that the association constant (Kass) of3/C60(48.1 ± 7.9M−1) was larger than that of2/C60(13.7 ± 1.4M−1).The formation of the 1:1 binding complexes2/C60and3/C60was also confirmed by MALDI-TOF mass spectrometry. Theoretical calculations suggest that2and3have appropriate cavities to embrace C60. These findings indicate that not only the π/π interaction between the fluorene moieties and the C60surface but also the CH/π interaction between the octyl groups and the C60surface serve efficiently in the supramolecular complexation with C60.