Triptycene-Based Molecular Rods for Langmuir-Blodgett Monolayers

0556491 - ÚOCHB 2023 RIV DE eng J - Journal Article
Kaletová, Eva - Santos Hurtado, Carina - Císařová, I. - Teat, S. J. - Kaleta, Jiří
Triptycene-Based Molecular Rods for Langmuir-Blodgett Monolayers.
ChemPlusChem. Roč. 87, č. 4 (2022), č. článku e202200023. ISSN 2192-6506. E-ISSN 2192-6506
R&D Projects: GA ČR(CZ) GA20-13745S
Research Infrastructure: e-INFRA CZ - 90140
Institutional support: RVO:61388963
Keywords : Langmuir-Blogdett monolayers * molecular devices * molecular rods * self-assembly * triptycene
OECD category: Organic chemistry
Impact factor: 3.4, year: 2022
Method of publishing: Limited access
https://doi.org/10.1002/cplu.202200023

Herein we introduce fully modular synthesis leading to three representative examples of rigid molecular rods that are intended to form sturdy monolayers on various surfaces. These molecules contain two triptycene units that are designed to interlock into a compact “double-decker“ structure. Two of the three final products provided suitable crystals for X-ray diffraction (analyzed on synchrotron), allowing deeper insight into packing in the 3-D crystal lattice. The acidity of all three compounds were determined by capillary electrophoresis, and the pK(a) values ranged between 2.06-2.53. All three rigid rods easily formed Langmuir-Blodgett monolayers (LBMs) on the water-air interfaces, with the area per molecule equal to 55-59 angstrom(2)/molecule, suggesting tight intermolecular packing. The thickness of all three films reached similar to 19 angstrom after transfer to a gold (111) surface, meaning that individual molecules are tilted maximally 38 degrees from the axis perpendicular to the surface. The structure of one of these films on a gold (111) surface was visualized by AFM. These geometrically unique molecules represent promising platforms with a wide scope of applicability in the supramolecular architecture.
Permanent Link: http://hdl.handle.net/11104/0330710


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