Molecular Spoked Wheels: Synthesis and Self-Assembly Studies on Rigid Nanoscale 2D Objects

被引：20

作者：

Aggarwal, A. Vikas ^{[1
]}

Jester, Stefan-S ^{[1
]}

Taheri, Sara Mehdizadeh ^{[2
]}

Foerster, Stephan ^{[2
]}

Hoeger, Sigurd ^{[1
]}

机构：

[1] Univ Bonn, Kekule Inst Organ Chem & Biochem, D-53121 Bonn, Germany

[2] Univ Bayreuth, D-95440 Bayreuth, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2013年 / 19卷 / 14期

关键词：

aggregation; aromatic compounds; macrocycles; nanostructures; template synthesis; SHAPE-PERSISTENT MACROCYCLES; ARYLENE-ETHYNYLENE MACROCYCLES; LIMITED COLLOID AGGREGATION; COVALENT-TEMPLATE APPROACH; GRAPHDIYNE SUBSTRUCTURES; CARBON NETWORKS; PHOTOPHYSICAL PROPERTIES; SONOGASHIRA REACTIONS; EFFICIENT SYNTHESIS; INTEGRAL-EQUATIONS;

D O I：

10.1002/chem.201203444

中图分类号：

O6 [化学];

学科分类号：

070301 [无机化学];

摘要：

We present the efficient synthesis of a new molecular spoked-wheel structure (MSW-3). Two derivatives with diameters of approximately 4nm have been prepared. By highlighting the importance of pseudo-high-dilution conditions during cyclization, we were able to access the compounds on a several hundred milligram scale. In addition to the standard characterization (NMR spectroscopy, MS), we describe a detailed investigation of the optical properties of the fluorescent MSWs by comparison with appropriate model chromophores. Furthermore, a comprehensive study of the structure in solution by means of light- and X-ray scattering experiments has been conducted. Scanning tunneling microscopy (STM) revealed the two-dimensional organization of the molecules on highly oriented pyrolytic graphite and emphasized the spoked-wheel structure. The diameter of these molecules measured by small-angle X-ray scattering is in very good agreement with that obtained from STM and matches the results of molecular modeling. This confirms the rigidifying effect of the spokes, which results in highly shape-persistent nanometer-sized oblate organic compounds.

引用

页码：4480 / 4495

页数：16

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