Controllable Orientation of Ester-Group-Induced Intermolecular Halogen Bonding in a 2D Self-Assembly

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• 作者：Bao Zha ; Meiqiu Dong ; Xinrui Miao ; Kai Miao ; Yi Hu ; Yican Wu ; Li Xu ; Wenli Deng
• 刊名：The Journal of Physical Chemistry Letters
• 出版年：2016
• 出版时间：August 18, 2016
• 年：2016
• 卷：7
• 期：16
• 页码：3164-3170
• 全文大小：684K
• 年卷期：0
• ISSN：1948-7185

文摘

Halogen bonding with high specificity and directionality in the geometry has proven to be an important type of noncovalent interaction to fabricate and control 2D molecular architectures on surfaces. Herein, we first report how the orientation of the ester substituent for thienophenanthrene derivatives (5,10-DBTD and 5,10-DITD) affects positive charge distribution of halogens by density functional theory, thus determining the formation of an intermolecular halogen bond and different self-assembled patterns by scanning tunneling microscopy. The system presented here mainly includes heterohalogen X···O═C and X···S halogen bonds, H···Br and H···O hydrogen bonds, and I···I interaction, where the directionality and strength of such weak bonds determine the molecular arrangement by varying the halogen substituent. This study provides a detailed understanding of the role of ester orientation, concentration, and solvent effects on the formation of halogen bonds and proves relevant for identification of multiple halogen bonding in supramolecular chemistry.