Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India.
J Org Chem. 2012 Sep 21;77(18):7858-65. doi: 10.1021/jo3010292. Epub 2012 Sep 4.
Pyrene-tetraphenol TP2 constitutes a molecular system with inherent features for inclusion of two or more guest molecules that are complementary in terms of size and shape. Hydrogen-bonded self-assembly of TP2 in the solid state is shown to lead to voids within which the guest molecules are incorporated. A large aromatic expanse extant to the pyrene core in TP2 permits inclusion of two different types of guest species interchangeably. The robust association manifests in packing equivalence in all of the inclusion compounds of TP2 with the exception of the compound formed with pyridine and o-dichlorobenzene guests; in the latter, pyridine terminates the otherwise 3-dimensional hydrogen-bonded organization. The half-component of TP2, i.e., 4,6-bis(4-hydroxyphenyl)-m-xylene (BX), deduced by simple structural reduction, is shown to exhibit guest inclusion, but with considerably less guest accessible volume. The limited yet meaningful set of guests allows mimicry of the two expected patterns of molecular organization based on hydrogen bonding for both TP2 and BX in the solid state.
芘-四苯醇 TP2 构成了一个分子系统，具有内在的特征，可以包含两个或更多在大小和形状上互补的客体分子。TP2 在固态中的氢键自组装被证明会导致形成空腔，客体分子被包含在其中。TP2 中芘核心周围存在的大芳香区域允许两种不同类型的客体物种交替包含。这种牢固的缔合表现为所有包含 TP2 的化合物在包装上都是等价的，除了与吡啶和邻二氯苯客体形成的化合物；在后一种情况下，吡啶终止了否则是三维氢键组织。TP2 的半组分，即 4,6-双（4-羟基苯基）-间二甲苯（BX），通过简单的结构还原推断出，表现出客体包含，但可及的客体体积要小得多。有限但有意义的客体集允许模拟基于氢键的两种预期的分子组织模式，既适用于 TP2 也适用于 BX 在固态中的情况。
