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Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization
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JoVE Journal Chemistry
Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

Photogeneration of N-Heterocyclic Carbenes: Application in Photoinduced Ring-Opening Metathesis Polymerization

DOI:
10.3791/58539-v

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12:19 min

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November 29, 2018

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, , , , , , ,
1ICGM, Université de Montpellier, CNRS, ENSCM, 2Institut de Science des Matériaux de Mulhouse (IS2M UMR 7361 CNRS),Université de Haute-Alsace, 3Université de Strasbourg, 4Laboratoire de Chimie des Polymères Organiques (LCPO UMR 5629 ENSCBP),Université de Bordeaux

Chapters

  • 00:04Title
  • 01:12Synthesis of 1,3-Dimesitylimidazolium Tetraphenylborate (IMesH+BPh4‐)
  • 02:49Photogeneration of 1,3-Dimesitylimidazol-2-ylidene (IMes) and Formation of the 1,3-Dimesitylimidazolium-2-dithiocarboxylate Adduct (IMes-CS2)
  • 04:13Spectrophotometric Titration of Photogenerated IMes
  • 06:12Photoinduced Ring-Opening Metathesis Polymerization (PhotoROMP) of Norbornene (NB) in Miniemulsion
  • 09:29Results: Characterization of N-Heterocyclic Carbene (NHC) Products
  • 11:35Conclusion

Summary

Automatic Translation

Automatic Translation

We describe a protocol to photogenerate N-heterocyclic carbenes (NHCs) by UV irradiation of a 2-isopropylthioxanthone/imidazolium tetraphenylborate salt system. Methods to characterize the photoreleased NHC and elucidate the photochemical mechanism are proposed. The protocols for ring-opening metathesis photopolymerization in solution and miniemulsion illustrate the potential of this 2-component NHC photogenerating system.

Tags

Keywords: N-Heterocyclic CarbenesNHCPhotolatent NHCPhotoinduced Ring-Opening Metathesis PolymerizationImidazolium SaltsPhotochemistrySpectrophotometric TitrationPhenol RedNorborneneMiniemulsionRuthenium Precatalyst

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