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Nuermaimaiti A, Ning Y, Cramer JL, et al. Influence of CH···N Interaction in the Self-Assembly of an Oligo(isoquinolyne-ethynylyne) Molecule with Distinct Conformational States. Langmuir. 2017;33(41):10782-10791doi: 10.1021/acs.langmuir.7b02207.
Nuermaimaiti, A., Ning, Y., Cramer, J. L., Svane, K. L., Hammer, B., Gothelf, K. V., & Linderoth, T. R. (2017). Influence of CH···N Interaction in the Self-Assembly of an Oligo(isoquinolyne-ethynylyne) Molecule with Distinct Conformational States. Langmuir : the ACS journal of surfaces and colloids, 33(41), 10782-10791. https://doi.org/10.1021/acs.langmuir.7b02207
Nuermaimaiti, Ajiguli, et al. "Influence of CH···N Interaction in the Self-Assembly of an Oligo(isoquinolyne-ethynylyne) Molecule with Distinct Conformational States." Langmuir : the ACS journal of surfaces and colloids vol. 33,41 (2017): 10782-10791. doi: https://doi.org/10.1021/acs.langmuir.7b02207
Nuermaimaiti A, Ning Y, Cramer JL, Svane KL, Hammer B, Gothelf KV, Linderoth TR. Influence of CH···N Interaction in the Self-Assembly of an Oligo(isoquinolyne-ethynylyne) Molecule with Distinct Conformational States. Langmuir. 2017 Oct 17;33(41):10782-10791. doi: 10.1021/acs.langmuir.7b02207. Epub 2017 Oct 02. PMID: 28968110.
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Langmuir. 2017 Oct 17;33(41):10782-10791. doi: 10.1021/acs.langmuir.7b02207. Epub 2017 Oct 02.

Influence of CH···N Interaction in the Self-Assembly of an Oligo(isoquinolyne-ethynylyne) Molecule with Distinct Conformational States.

Langmuir : the ACS journal of surfaces and colloids

Ajiguli Nuermaimaiti, Yanxiao Ning, Jacob L Cramer, Katrine L Svane, Bjørk Hammer, Kurt V Gothelf, Trolle R Linderoth

Affiliations

  1. Interdisciplinary Nanoscience Center (iNANO), Aarhus University , 8000 Aarhus C, Denmark.
  2. Department of Chemistry, Aarhus University , 8000 Aarhus C, Denmark.
  3. Department of Physics and Astronomy, Aarhus University , 8000 Aarhus C, Denmark.

PMID: 28968110 DOI: 10.1021/acs.langmuir.7b02207

Abstract

Molecular conformational flexibility can play an important role in supramolecular self-assembly on surfaces, affecting not least chiral molecular assemblies. To explicitly and systematically investigate the role of molecular conformational flexibility in surface self-assembly, we synthesized a three-bit conformational switch where each of three switching units on the molecules can assume one of two distinct binary positions on the surface. The molecules are designed to promote C-H···N type hydrogen bonds between the switching units. While supramolecular self-assembly based on strong hydrogen-bonding interactions has been widely explored, less is known about the role of such weaker directional interactions for surface self-assembly. The synthesized molecules consist of three nitrogen-containing isoquinoline (IQ) bits connected by ethynylene spokes and terminated by tert-butyl (tBu) groups. Using high-resolution scanning tunnelling microscopy, we investigate the self-assembly of the IQ-tBu molecules on a Au(111) surface under ultrahigh-vacuum conditions. The molecules form extended domains of brick-wall structure where the molecular backbones are packed regularly but without selection of specific molecular conformations. However, statistical analysis of the extended network demonstrates alignment/correlation for the orientations of the switching units indicating specific interactions. The primary interaction motifs in the structure are quantified from DFT calculations, showing that the brick-wall structure is indeed stabilized by two types of weak C-H···N bonds, involving either aromatic hydrogens on the IQ groups or nonaromatic hydrogens on the tBu groups. Analysis of the C-H···N interactions in the brick-wall structure explains the observed distribution and alignment of molecular conformations as well as the overall organization of the molecular surface structures.

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