Geometry Symmetry of Conjugated Cores along C–Br Bond Effect on the 2D Self-Assembly by Intermolecular H···Br and Br···Br Bonds

Jinxing Li 1 Juntian Wu 1 Siwei Chen 2 Xinrui Miao 3 Fabien Silly 3 Wenli Deng 1
1 South University of Science and Technology of China
2 Central South University [Changsha]
3 LEPO - Laboratoire d'Electronique et nanoPhotonique Organique
SPEC - UMR3680 - Service de physique de l'état condensé, IRAMIS - Institut Rayonnement Matière de Saclay
Abstract : Supramolecular self-assemblies of bromine substituted benzene and naphthalene derivatives (Br-BC16 and Br-NC16) are investigated using scanning tunneling microscopy at the liquid-solid interface. These two molecules arrange in different linear patterns stabilized by intermolecular H···Br and Br···Br bonds. Due to the different geometry symmetry of conjugated cores along the C–Br bond, the side chains and conjugated cores of Br-BC16 pack with the same direction; however, the side chains of Br-NC16 stretch into different directions along the graphite lattices and the conjugated cores of Br-NC16 in each dimer adopt the reverse orientation. Electrostatic potential (ESP) maps and density functional theory (DFT) calculations show that a pair of intermolecular H···Br bonds between the hydrogen atoms with the positive charge and the bromine atoms with the negative charge in each dimer dominate the structural formation. In addition, a Br···Br bond in each dimer for Br-BC16 and a Br···Br bond between the neighboring dimers for Br-NC16 are formed to stabilize the nanostructures. The results provide insights into the understanding of molecular self-assembly at the liquid-solid interface through the hydrogen bond or the halogen bond for bromine substituted molecules.
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Article dans une revue
The Journal of Physical Chemistry C, ACS American Chemical Society - Publications, 2018, 122 (27), pp.15338 - 15343. 〈10.1021/acs.jpcc.8b02730〉
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https://hal.archives-ouvertes.fr/hal-01872126
Contributeur : Dominique Girard <>
Soumis le : mardi 11 septembre 2018 - 16:17:14
Dernière modification le : jeudi 13 septembre 2018 - 01:10:19

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DSM-IRAMIS | CEA | IRAMIS-SPEC | CEA-UPSAY | CEA-DRF | UNIV-PARIS-SACLAY

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Jinxing Li, Juntian Wu, Siwei Chen, Xinrui Miao, Fabien Silly, et al.. Geometry Symmetry of Conjugated Cores along C–Br Bond Effect on the 2D Self-Assembly by Intermolecular H···Br and Br···Br Bonds. The Journal of Physical Chemistry C, ACS American Chemical Society - Publications, 2018, 122 (27), pp.15338 - 15343. 〈10.1021/acs.jpcc.8b02730〉. 〈hal-01872126〉

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