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Steering On-Surface Reactions by a Self-Assembly Approach.

Qiwei Chen1, Jacob R Cramer2, Jing Liu1

  • 1BNLMS, College of Chemistry and Molecular Engineering, Peking University, Beijing, 100871, China.

Angewandte Chemie (International Ed. in English)
|March 25, 2017
PubMed
Summary

Self-assembly of 4,4'-Bis(2,6-difluoropyridin-4-yl)-1,1':4',1''-terphenyl (BDFPTP) molecules on gold surfaces enhances reaction control. This strategy improves regioselectivity and suppresses unwanted side reactions in surface chemistry.

Keywords:
dehydrocyclizationdensity functional theoryon-surface reactionscanning tunneling microscopeself-assembly

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Area of Science:

  • Surface Chemistry
  • Materials Science
  • Organic Synthesis

Background:

  • Controlling chemical reactions on surfaces is crucial for developing new materials and devices.
  • On-surface reactions offer unique pathways for molecular assembly and functionalization.
  • Achieving high selectivity in these reactions remains a significant challenge.

Purpose of the Study:

  • To investigate the role of molecular self-assembly in directing on-surface chemical reactions.
  • To explore the dehydrocyclization and covalent coupling of 4,4 -Bis(2,6-difluoropyridin-4-yl)-1,1 :4 ',1 ''-terphenyl (BDFPTP) on Au(111).
  • To demonstrate a strategy for enhancing reaction regioselectivity through pre-reaction molecular organization.

Main Methods:

  • Scanning Tunneling Microscopy (STM) for atomic-scale visualization of molecular arrangements and reactions.
  • Density Functional Theory (DFT) calculations to understand reaction mechanisms and energetics.
  • Utilizing self-assembly of BDFPTP molecules into well-defined domains on Au(111) prior to reaction.

Main Results:

  • Observed dehydrocyclization and covalent coupling of BDFPTP molecules on Au(111).
  • Demonstrated that pre-formed molecular domains significantly enhance the regioselectivity of the dehydrocyclization.
  • Showed suppression of undesired defluorinated coupling pathways due to controlled self-assembly.

Conclusions:

  • Self-assembly is an effective strategy to precisely control on-surface chemical reactions.
  • Molecular organization prior to reaction can steer reactivity and improve product selectivity.
  • This approach holds significant potential for designing complex molecular architectures on surfaces.