Selective Adsorption of Coronene atop the Polycyclic Aromatic Diimide Monolayer Investigated by STM and DFT

The self-assemblies of polycyclic aromatic diimide (PAI) compounds on solid surfaces have attracted great interest because of the versatile and attractive properties for application in organic electronics. Here, a planar guest species (coronene) selectively adsorbs on the helicene-typed PAI1 monolayer strongly, depending on the conjugated cores of these PAIs. PAI1 molecule displays evidently a bowl structure lying on the highly oriented pyrolytic graphite surface due to the torsion of the “C”-shaped fused benzene rings. In combination with density functional theory calculation, the selective inclusion of coronene atop the backbone of the PAI1 array might be attributed to the bowl structure, which provides a groove for immobilizing coronene molecules. On the other planar densely packed arrays, it is difficult to observe the unstable adsorption of coronene. The selective addition of coronene molecules would be a strategic step toward the controllable multicomponent supramolecular architectures.

[1]  Q. Zeng,et al.  Formation of Coronene Clusters in Concentration and Temperature Controlled Two-Dimensional Porous Network. , 2016, ACS applied materials & interfaces.

[2]  Ke Deng,et al.  A size, shape and concentration controlled self-assembling structure with host-guest recognition at the liquid-solid interface studied by STM. , 2016, Nanoscale.

[3]  S. De Feyter,et al.  Periodic Functionalization of Surface-Confined Pores in a Two-Dimensional Porous Network Using a Tailored Molecular Building Block. , 2016, ACS nano.

[4]  X. Yang,et al.  Syntheses of polycyclic aromatic diimides via intramolecular cyclization of maleic acid derivatives , 2016 .

[5]  Junyong Zhang,et al.  Solution concentration controlled self-assembling structure with host-guest recognition at the liquid-solid interface. , 2015, Physical chemistry chemical physics : PCCP.

[6]  Q. Zeng,et al.  Site-selection and adaptive reconstruction in a two-dimensional nanoporous network in response to guest inclusion , 2015 .

[7]  K. W. Hipps,et al.  Effect of dispersion on surface interactions of cobalt(II) octaethylporphyrin monolayer on Au(111) and HOPG(0001) substrates: a comparative first principles study. , 2014, Physical chemistry chemical physics : PCCP.

[8]  K. Horn,et al.  Long-Range Order in an Organic Overlayer Induced by Surface Reconstruction: Coronene on Ge(111) , 2014 .

[9]  W. Xu,et al.  Adlayer Structure of Shape-Persistent Macrocycle Molecules: Fabrication and Tuning Investigated with Scanning Tunneling Microscopy , 2014 .

[10]  F. Rosei,et al.  Two-dimensional self-assembly of a symmetry-reduced tricarboxylic acid. , 2013, Langmuir : the ACS journal of surfaces and colloids.

[11]  W. Piskorz,et al.  Supramolecular ordering of PTCDA molecules: the key role of dispersion forces in an unusual transition from physisorbed into chemisorbed state. , 2012, ACS nano.

[12]  K. Horn,et al.  Ge(001) as a template for long-range assembly of π-stacked coronene rows. , 2012, Langmuir : the ACS journal of surfaces and colloids.

[13]  N. Martsinovich,et al.  Incorporation dynamics of molecular guests into two-dimensional supramolecular host networks at the liquid-solid interface. , 2011, Langmuir : the ACS journal of surfaces and colloids.

[14]  Q. Zeng,et al.  Heterogeneous bilayer molecular structure at a liquid-solid interface. , 2011, Nanoscale.

[15]  W. Xu,et al.  Molecular adlayer and photo-induced structural transformation of a diarylethene derivative on Au(1 1 1) investigated with scanning tunneling microscopy , 2011 .

[16]  Yeliang Wang,et al.  Tuning structural and mechanical properties of two-dimensional molecular crystals: the roles of carbon side chains. , 2011, Nano letters (Print).

[17]  Chuan-feng Chen,et al.  Synthesis and structures of multifunctionalized helicenes and dehydrohelicenes: an efficient route to construct cyan fluorescent molecules. , 2010, Chemistry.

[18]  L. Wan,et al.  Solvent-controlled 2D host-guest (2,7,12-trihexyloxytruxene/coronene) molecular nanostructures at organic liquid/solid interface investigated by scanning tunneling microscopy. , 2010, Langmuir : the ACS journal of surfaces and colloids.

[19]  S. De Feyter,et al.  Two-dimensional supramolecular self-assembly: nanoporous networks on surfaces. , 2009, Chemical Society reviews.

[20]  Xiang Lin,et al.  Directing two-dimensional molecular crystallization using guest templates. , 2008, Chemical communications.

[21]  N. Richardson.  Adsorption-induced chirality in highly symmetric hydrocarbon molecules: lattice matching to substrates of lower symmetry , 2007 .

[22]  Q. Zeng,et al.  Coadsorption-induced reconstruction of supramolecular assembly characteristics. , 2007, Chemphyschem : a European journal of chemical physics and physical chemistry.

[23]  M. van der Auweraer,et al.  Structural transformation of a two-dimensional molecular network in response to selective guest inclusion. , 2007, Angewandte Chemie.

[24]  O. Ito,et al.  Epitaxial supramolecular assembly of fullerenes formed by using a coronene template on a Au(111) surface in solution. , 2007, Journal of the American Chemical Society.

[25]  L. Wan,et al.  Effect of polycyclic aromatic hydrocarbons on detection sensitivity of ultratrace nitroaromatic compounds. , 2007, Analytical chemistry.

[26]  F. D. De Schryver,et al.  Two-dimensional porous molecular networks of dehydrobenzo[12]annulene derivatives via alkyl chain interdigitation. , 2006, Journal of the American Chemical Society.

[27]  L. Douillard,et al.  Selectivity of Single‐Molecule Dynamics in 2D Molecular Sieves , 2006 .

[28]  L. Wan,et al.  Controllable distribution of single molecules and peptides within oligomer template investigated by STM. , 2006, Journal of the American Chemical Society.

[29]  L. Douillard,et al.  Single-molecule dynamics in a self-assembled 2D molecular sieve. , 2006, Nano letters.

[30]  Stefan J H Griessl,et al.  Molecular structures on crystalline metallic surfaces - From STM images to molecular electronics , 2005 .

[31]  K. Itaya,et al.  Effect of underlying coronene and perylene adlayers for [60]fullerene molecular assembly. , 2005, Chemical communications.

[32]  K. W. Hipps,et al.  Supramolecular structures of coronene and alkane acids at the Au(111)-solution interface: a scanning tunneling microscopy study. , 2005, Langmuir : the ACS journal of surfaces and colloids.

[33]  Michael Hietschold,et al.  Incorporation and manipulation of coronene in an organic template structure. , 2004, Langmuir : the ACS journal of surfaces and colloids.

[34]  L. Wan,et al.  Template-Induced Inclusion Structures with Copper(II) Phthalocyanine and Coronene as Guests in Two-Dimensional Hydrogen-Bonded Host Networks , 2004 .

[35]  F. D. Schryver,et al.  Two-dimensional supramolecular self-assembly probed by scanning tunneling microscopy , 2003 .

[36]  K. Walzer,et al.  Formation and characterization of coronene monolayers on HOPG(0001) and MoS2(0001): a combined STM/STS and tight-binding study , 1998 .

[37]  Burke,et al.  Generalized Gradient Approximation Made Simple. , 1996, Physical review letters.

[38]  N. Champness,et al.  Guest-induced growth of a surface-based supramolecular bilayer. , 2011, Nature chemistry.