scholarly journals Self-assembled monolayers of shape-persistent macrocycles on graphite: interior design and conformational polymorphism

2014 ◽  
Vol 10 ◽  
pp. 2774-2782 ◽  
Author(s):  
Joscha Vollmeyer ◽  
Friederike Eberhagen ◽  
Sigurd Höger ◽  
Stefan-S Jester

Three shape-persistent naphthylene–phenylene–acetylene macrocycles of identical backbone structures and extraannular substitution patterns but different (empty, apolar, polar) nanopore fillings are self-assembled at the solid/liquid interface of highly oriented pyrolytic graphite and 1,2,4-trichlorobenzene. Submolecularly resolved images of the resulting two-dimensional (2D) crystalline monolayer patterns are obtained by in situ scanning tunneling microscopy. A concentration-dependent conformational polymorphism is found, and open and more dense packing motifs are observed. For all three compounds alike lattice parameters are found, therefore the intermolecular macrocycle distances are mainly determined by their size and symmetry. This is an excellent example that the graphite acts as a template for the macrocycle organization independent from their specific interior.

2014 ◽  
Vol 10 ◽  
pp. 2783-2788 ◽  
Author(s):  
Stefan-S Jester ◽  
A Vikas Aggarwal ◽  
Daniel Kalle ◽  
Sigurd Höger

Self-assembled monolayers of a molecular spoked wheel (a shape-persistent macrocycle with an intraannular spoke/hub system) and its synthetic precursor are investigated by scanning tunneling microscopy (STM) at the liquid/solid interface of 1-octanoic acid and highly oriented pyrolytic graphite. The submolecularly resolved STM images reveal that the molecules indeed behave as more or less rigid objects of certain sizes and shapes – depending on their chemical structures. In addition, the images provide insight into the multilayer growth of the molecular spoked wheels (MSWs), where the first adlayer acts as a template for the commensurate adsorption of molecules in the second layer.


2007 ◽  
Vol 121-123 ◽  
pp. 495-498 ◽  
Author(s):  
Jun Hyung Park ◽  
Buyng Su Park ◽  
Gu Huh ◽  
Seung Hyun Lee ◽  
Hyun Sook Lee ◽  
...  

We report on the distribution of mixed self-assembled monolayers (SAMs) composed of biotinylated and diluent alkylthiolates for streptavidin immobilization. Two thiol derivatives, 11-mercapto-1-undecanol (MUOH) and 11-mercaptoundecanoic-(8-biotinylamido-3,6-dioxaoctyl) amide (MBDA), were employed for mixed SAM. These thiols formed self-assembled monolayer without local domain, and streptavidins were immobilized onto biotinylated gold surface without nonspecific binding. In order to find the optimized condition of immobilization of streptavidin, we controlled the mixing ratio of two kind thiols by colorimetric detection assay, and the immobilization was characterized by atomic force microscopy (AFM), scanning tunneling microscopy (STM), and ellipsometer.


Langmuir ◽  
2008 ◽  
Vol 24 (12) ◽  
pp. 5984-5987 ◽  
Author(s):  
Sangyeob Lee ◽  
Sung-Soo Bae ◽  
Gilberto Medeiros-Ribeiro ◽  
Jason J. Blackstock ◽  
Sehun Kim ◽  
...  

2019 ◽  
Vol 55 (58) ◽  
pp. 8426-8429 ◽  
Author(s):  
Catherine Adam ◽  
Lara Faour ◽  
Valérie Bonnin ◽  
Tony Breton ◽  
Eric Levillain ◽  
...  

Helical foldamers were incorporated in self-assembled monolayers that successfully transduce host–guest binding events.


2017 ◽  
Vol 204 ◽  
pp. 215-231 ◽  
Author(s):  
Iris Destoop ◽  
Andrea Minoia ◽  
Oleksandr Ivasenko ◽  
Aya Noguchi ◽  
Kazukuni Tahara ◽  
...  

Chiral induction in self-assembled monolayers has garnered considerable attention in the recent past, not only due to its importance in chiral resolution and enantioselective heterogeneous catalysis but also because of its relevance to the origin of homochirality in life. Here, we demonstrate the emergence of homochirality in a supramolecular low-density network formed by achiral molecules at the interface of a chiral solvent and an atomically-flat achiral substrate. We focus on the impact of structure and functionality of the adsorbate and the chiral solvent on the chiral induction efficiency in self-assembled physisorbed monolayers, as revealed by scanning tunneling microscopy. Different induction mechanisms are proposed and evaluated, with the assistance of advanced molecular modeling simulations.


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