ExBox: A Polycyclic Aromatic Hydrocarbon Scavenger
详细信息 查看全文
- 作者：Jonathan C. Barnes ; Michal Jur铆膷ek ; Nathan L. Strutt ; Marco Frasconi ; Srinivasan Sampath ; Marc A. Giesener ; Psaras L. McGrier ; Carson J. Bruns ; Charlotte L. Stern ; Amy A. Sarjeant ; J. Fraser Stoddart
- 刊名：The Journal of the American Chemical Society
- 出版年：2013
- 出版时间：January 9, 2013
- 年：2013
- 卷：135
- 期：1
- 页码：183-192
- 全文大小：631K
- 年卷期：v.135,no.1(January 9, 2013)
- ISSN：1520-5126
文摘
A template-directed protocol, which capitalizes on donor鈥揳cceptor interactions, is employed to synthesize a semi-rigid cyclophane (ExBox4+) that adopts a box-like geometry and is comprised of 蟺-electron-poor 1,4-phenylene-bridged (鈥渆xtended鈥? bipyridinium units (ExBIPY2+). ExBox4+ functions as a high-affinity scavenger of an array of different polycyclic aromatic hydrocarbons (PAHs), ranging from two to seven fused rings, as a result of its large, accommodating cavity (approximately 3.5 脜 in width and 11.2 脜 in length when considering the van der Waals radii) and its ability to form strong non-covalent bonding interactions with 蟺-electron-rich PAHs in either organic or aqueous media. In all, 11 PAH guests were observed to form inclusion complexes with ExBox4+, with coronene being the largest included guest. Single-crystal X-ray diffraction data for the 11 inclusion complexes ExBox4+PAH as well as UV/vis spectroscopic data for 10 of the complexes provide evidence of the promiscuity of ExBox4+ for the various PAHs. Nuclear magnetic resonance spectroscopy and isothermal titration calorimetric analyses of 10 of the inclusion complexes are employed to further characterize the host鈥揼uest interactions in solution and determine the degree with which ExBox4+ binds each PAH compound. As a proof-of-concept, a batch of crude oil from Saudi Arabia was subjected to extraction with the water-soluble form of the PAH receptor, ExBox路4Cl, resulting in the isolation of different aromatic compounds after ExBox路4Cl was regenerated.