Formation and control of porous two-dimensional molecular self-assembly at solid-liquid interfaces

Yoshito Tobe*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

2 Scopus citations

Abstract

Two-dimensional (2D) architectures, particularly porous molecular networks, on solid surfaces formed via self-assembly have received a great deal of interest because of the prospective applications in optoelectronics and tailor-made catalysis. We found that porous 2D molecular networks were formed at liquid-solid interfaces, typically an organic solvent/graphite or Au(111),by triangle-shaped phenylene-ethynylene macrocycles, dehydrobenzo[12]annulenes (DBAs),via their self-assembly by van der Waals interactions between the interdigitated alkyl chains attached to the periphery of the macrocyclic core. Factors that led to the preferential formation of porous, honeycomb-shaped networks were elucidated including the size of the π-conjugated cores, alkyl chain length, solvent, concentration, temperature, and solid substrates. Not only homochiral molecular networks were achieved by self-assembly of DBAs with chiral side chains, but also network homochirality was induced by addition of a small amount of a chiral DBA into an achiral DBA as a chirality inducer. Co-adsorption of guest molecules in the pores occurred through recognition of the size and shape, leading to selective inclusion of homo-molecular as well as hetero-molecular clusters into the nanowells. Moreover, the interior of the pores was functionalized for tailored molecular recognition toward advanced use of 2D molecular networks on surfaces.

Original languageEnglish
Pages (from-to)1255-1266
Number of pages12
JournalYuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry
Volume70
Issue number12
DOIs
StatePublished - 1 Dec 2012

Keywords

  • Catalysis
  • Co-adsorption
  • Guest inclusion
  • Molecular electronics
  • Molecular network
  • Nanowell
  • On-surface chirality
  • Scanning tunneling microscopy
  • Self-assembly
  • Solid-liquid interface

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