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Synlett 2023; 34(14): 1689-1693
DOI: 10.1055/a-1988-1984
letter
Published as part of the Special Section 13th EuCheMS Organic Division Young Investigator Workshop

Mesyl and Triflyl Functionalized N-Heterocyclic Carbenes as Acceptor Fragments in Luminescent Carbene-Metal-Amide Complexes

Armands Ruduss
a   Institute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena Str., Riga 1048, Latvia
,
Zanis Sisojevs
a   Institute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena Str., Riga 1048, Latvia
,
Sergey Belyakov
b   Latvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga 1006, Latvia
,
Kaspars Traskovskis  ∗
a   Institute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena Str., Riga 1048, Latvia
› Author AffiliationsThis research was funded by the Latvian Council of Science (Latvijas Zinātnes Padome; lzp-2019/1-0231).
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Abstract

Synthetic procedures providing access to mesyl and triflyl functionalized derivatives of 1,3-bis(2,6-diisopropylphenyl)imidazolidin-2-ylidene (SIPr) have been provided in detail. New luminescent carbene-metal-amide (CMA) Cu(I) complexes based on acceptor group functionalized SIPr have been prepared. The effect of the LUMO energy in the sulfonyl functionalized N-heterocyclic carbene (NHC) series on the emissive properties of the CMAs has been investigated.

Key words

N-heterocyclic carbenes - acceptor groups - carbene-metal-amides - copper(I) complexes - luminescence

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1988-1984.
  • Supporting Information


Publication History

Received: 02 November 2022

Accepted after revision: 27 November 2022

Accepted Manuscript online:
27 November 2022

Article published online:
19 December 2022

© 2022. Thieme. All rights reserved

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  • 19 Compound 19a: To a solution of 9H-carbazole (0.093 g, 0.556 mmol) in anhydrous degassed THF (45 mL), KOtBu (0.063 g, 0.561 mmol) was added and the mixture was stirred at r.t. for 30 min. Then compound 18a (0.300 g, 0.465 mmol) was added and the mixture was stirred for an additional 3 h. Then mixture was filtered via syringe filter into anhydrous degassed hexane (250 mL) to precipitate the product. The obtained mixture was filtered and washed with hexane (50 mL) to obtain the product as an off-white solid. Yield: 0.234 g (65%). 1H NMR (DMSO-d 6, 500 MHz): δ = 8.04 (s, 4 H), 7.76 (d, J = 7.5 Hz, 2 H), 6.83 (t, J = 7.5 Hz, 2 H), 6.73 (t, J = 7.3 Hz, 2 H), 5.83 (d, J = 8.1 Hz, 2 H), 4.36 (s, 4 H), 3.43 (s, 6 H), 3.35 (m, 4 H), 1.42 (d, J = 6.7 Hz, 12 H), 1.27 (d, J = 6.7 Hz, 12 H). 13C NMR (DMSO-d 6, 125.77 MHz): δ = 202.70, 149.15, 148.86, 142.41, 138.90, 123.32, 123.24, 123.03, 118.98, 115.15, 112.99, 53.56, 43.17, 28.59, 24.63, 23.19. A similar method was used for the synthesis of compounds 19b and 20a (see the Supporting Information).
  • 20 CCDC 2214035 (19a) and 2214034 (20a) contain the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/structures