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共面有机点击笼嵌入多环芳烃。

Cofacial Organic Click Cage to Intercalate Polycyclic Aromatic Hydrocarbons.

机构信息

Organic and Medicinal Chemistry Division, CSIR-Indian Institute of Chemical Biology , 4, Raja S. C. Mullick Road, Kolkata 700032, India.

Academy of Scientific and Innovative Research (AcSIR) , 4, Raja S. C. Mullick Road, Kolkata 700032, India.

出版信息

Org Lett. 2016 Jul 15;18(14):3394-7. doi: 10.1021/acs.orglett.6b01554. Epub 2016 Jul 1.

DOI:10.1021/acs.orglett.6b01554
PMID:27367562
Abstract

The synthesis of a 3-fold symmetric cofacial organic cage (COC) through Cu(I)-catalyzed azide-alkyne cycloaddition is reported. The COC can function as an efficient receptor for carcinogenic polycyclic aromatic hydrocarbons to intercalate them in its intrinsic cavity through donor-acceptor and π···π stacking interactions. The association constants (Ka) are in the range of 3.7 × 10(4) to 1.3 × 10(6) M(-1). X-ray diffraction analysis authenticated that the polycyclic aromatic hydrocarbons (PAHs) are intercalated in the interior of the COC.

摘要

通过铜(I)催化的叠氮化物-炔烃环加成反应,合成了一种 3 重对称共面有机笼(COC)。该 COC 可以作为一种有效的致癌多环芳烃受体,通过供体-受体和 π···π 堆积相互作用将其插入其固有腔中。结合常数(Ka)在 3.7×10(4)至 1.3×10(6) M(-1)范围内。X 射线衍射分析证实多环芳烃(PAHs)插入 COC 的内部。

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