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

Armands Ruduss; Zanis Sisojevs; Sergey Belyakov; Kaspars Traskovskis

doi:10.1055/a-1988-1984

Synlett, Inhaltsverzeichnis

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

^aInstitute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena Str., Riga 1048, Latvia

,

Zanis Sisojevs

^aInstitute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena Str., Riga 1048, Latvia

,

Sergey Belyakov

^bLatvian Institute of Organic Synthesis, 21 Aizkraukles Str., Riga 1006, Latvia

,

Kaspars Traskovskis ∗

^aInstitute of Applied Chemistry, Faculty of Materials Science and Applied Chemistry, Riga Technical University, 3/7 Paula Valdena Str., Riga 1048, Latvia

› Institutsangaben

Abstract

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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

Volltext

Referenzen

References and Notes

1a Adachi C. Jpn. J. Appl. Phys. 2014; 53: 060101
1b Im Y, Kim M, Cho YJ, Seo J.-A, Yook KS, Lee JY. Chem. Mater. 2017; 29: 1946
1c Yang Z, Mao Z, Xie Z, Zhang Y, Liu S, Zhao J, Xu J, Chi Z, Aldred MP. Chem. Soc. Rev. 2017; 46: 915
1d Liu Y, Li C, Ren Z, Yan S, Bryce MR. Nat. Rev. Mater. 2018; 3: 18020
1e Huang T, Jiang W, Duan L. J. Mater. Chem. C 2018; 6: 5577

2 Endo A, Sato K, Yoshimura K, Kai T, Kawada A, Miyazaki H, Adachi C. Appl. Phys. Lett. 2011; 98: 083302

3a Di D, Romanov AS, Yang L, Richter JM, Rivett JP. H, Jones S, Thomas TH, Abdi Jalebi M, Friend RH, Linnolahti M, Bochmann M, Credgington D. Science 2017; 356: 159
3b Hamze R, Peltier JL, Sylvinson D, Jung M, Cardenas J, Haiges R, Soleilhavoup M, Jazzar R, Djurovich PI, Bertrand G, Thompson ME. Science 2019; 363: 601

4 Hamze R, Shi S, Kapper SC, Ravinson DS. M, Estergreen L, Jung MC, Tadle AC, Haiges R, Djurovich PI, Peltier JL, Jazzar R, Bertrand G, Bradforth SE, Thompson ME. J. Am. Chem. Soc. 2019; 141: 8616

5a Lüdtke N, Föller J, Marian CM. Phys. Chem. Chem. Phys. 2020; 22: 23530
5b Chotard F, Sivchik V, Linnolahti M, Bochmann M, Romanov AS. Chem. Mater. 2020; 32: 6114
5c Hamze R, Idris M, Ravinson DS. M, Jung M. c, Haiges R, Djurovich PI, Thompson ME. Front. Chem. 2020; 8: 401

6a Park IS, Lee SY, Adachi C, Yasuda T. Adv. Funct. Mater. 2016; 26: 1813
6b Chen T, Lu C.-H, Huang C.-W, Zeng X, Gao J, Chen Z, Xiang Y, Zeng W, Huang Z, Gong S, Wu C.-C, Yang C. J. Mater. Chem. C 2019; 7: 9087
6c Liu H, Li J, Li G, Zhang B, Zhan Q, Liu Z, Zhou C, Li K, Wang Z, Yang C. Dyes Pigm. 2020; 180: 108521
6d Yang D, Kim J.-M, Huh J.-S, Kim J.-J, Hong J.-I. Org. Electron. 2021; 95: 106187
6e Duda E, Hall D, Bagnich S, Carpenter-Warren CL, Saxena R, Wong MY, Cordes DB, Slawin AM. Z, Beljonne D, Olivier Y, Zysman-Colman E, Köhler A. J. Phys. Chem. B 2022; 126: 552

7a Wong MY, Krotkus S, Copley G, Li W, Murawski C, Hall D, Hedley GJ, Jaricot M, Cordes DB, Slawin AM. Z, Olivier Y, Beljonne D, Muccioli L, Moral M, Sancho-Garcia J.-C, Gather MC, Samuel ID. W, Zysman-Colman E. ACS Appl. Mater. Interfaces 2018; 10: 33360
7b Hundemer F, Graf von Reventlow L, Leonhardt C, Polamo M, Nieger M, Seifermann SM, Colsmann A, Bräse S. ChemistryOpen 2019; 8: 1413
7c Mubarok H, Lee W, Lee T, Jung J, Yoo S, Lee MH. Front. Chem. 2020; 8: 538

8a Shi S, Jung MC, Coburn C, Tadle A, Sylvinson DM. R, Djurovich PI, Forrest SR, Thompson ME. J. Am. Chem. Soc. 2019; 141: 3576
8b Romanov AS, Jones ST. E, Gu Q, Conaghan PJ, Drummond BH, Feng J, Chotard F, Buizza L, Foley M, Linnolahti M, Credgington D, Bochmann M. Chem. Sci. 2020; 11: 435
8c Conaghan PJ, Matthews CS. B, Chotard F, Jones ST. E, Greenham NC, Bochmann M, Credgington D, Romanov AS. Nat. Commun. 2020; 11: 1758
8d Ying A, Huang YH, Lu CH, Chen Z, Lee WK, Zeng X, Chen T, Cao X, Wu CC, Gong S, Yang C. ACS Appl. Mater. Interfaces 2021; 13: 13478
8e Reponen AM, Chotard F, Lempelto A, Shekhovtsev V, Credgington D, Bochmann M, Linnolahti M, Greenham NC, Romanov AS. Adv. Opt. Mater. 2022; 10: 2200312
8f Gu Q, Chotard F, Eng J, Reponen A.-PM, Vitorica-Yrezabal IJ, Woodward AW, Penfold TJ, Credgington D, Bochmann M, Romanov AS. Chem. Mater. 2022; 34: 7526

9a Meiries S, Speck K, Cordes DB, Slawin AM. Z, Nolan SP. Organometallics 2013; 32: 330
9b Le Duc G, Meiries S, Nolan SP. Organometallics 2013; 32: 7547
9c Yong X, Thurston R, Ho C.-Y. Synthesis 2019; 51: 2058

10a Ruduss A, Turovska B, Belyakov S, Stucere KA, Vembris A, Traskovskis K. Inorg. Chem. 2022; 61: 2174
10b Ruduss A, Sisojevs Z, Vembris A, Stucere KA, Traskovskis K. Proc. SPIE 2022; 12149: 1214908

11 Dorta R, Stevens ED, Scott NM, Costabile C, Cavallo L, Hoff CD, Nolan SP. J. Am. Chem. Soc. 2005; 127: 2485
12 Arduengo AJ, Krafczyk R, Schmutzler R, Craig HA, Goerlich JR, Marshall WJ, Unverzagt M. Tetrahedron 1999; 55: 14523
13 Leuthäußer S, Schwarz D, Plenio H. Chem. Eur. J. 2007; 13: 7195
14 Mete TB, Khopade TM, Bhat RG. Tetrahedron Lett. 2017; 58: 415
15 Billard T, Large S, Langlois BR. Tetrahedron Lett. 1997; 38: 65
16 Compound 18a: A mixture of 1,3-bis(2,6-diisopropyl-4-(methylthio)phenyl)-4,5-dihydro-1H-imidazol-3-ium chloride (16a) (2.00 g, 3.43 mmol) and KHMDS (0.72 g, 3.61 mmol) in anhydrous THF (200 mL) was stirred for 1 h at r.t. Then CuCl (0.34 g, 3.43 mmol) was added and the mixture was stirred for additional 2.5 h at r.t. The formed precipitate containing product was separated by filtration. The solid was collected and purified using a Soxhlet apparatus (24 h, solvent: acetonitrile) to afford the product as a greenish solid. Yield: 1.34 g (60%). ¹H NMR (DMSO-d ₆, 500 MHz): δ = 7.88 (s, 4 H), 4.16 (s, 4 H), 3.36 (s, 6 H), 3.18 (hept, J = 6.7 Hz, 4 H), 1.38 (d, J = 6.7 Hz, 12 H), 1.31 (d, J = 6.7 Hz, 12 H). ¹³C NMR data not obtained due to the low solubility of compound 18a.
17 Santoro O, Collado A, Slawin AM. Z, Nolan SP, Cazin CS. J. Chem. Commun. 2013; 49: 10483
18 Compound 18b: A mixture of 1,3-bis(2,6-diisopropyl-4-((trifluoromethyl)sulfonyl)phenyl)-4,5-dihydro-1H-imidazol-3-ium chloride (17b) (2.16 g, 3.13 mmol), CuCl (0.38 g, 3.84 mmol) and K₂CO₃ (0.70 g, 5.06 mmol) in acetone (200 mL) was stirred and heated at reflux for 24 h. The precipitate containing product was separated by filtration, washed with H₂O and dried at r.t. The solid was purified by using a Soxhlet apparatus (48 h, solvent: acetonitrile) to afford the product as a greenish solid. Yield: 1.72 g (73%). ¹H NMR (DMSO-d ₆, 500 MHz): δ = 8.03 (s, 2 H), 4.25 (s, 4 H), 3.24–3.20 (m, 4 H), 1.38 (d, J = 6.8 Hz, 12 H), 1.31 (d, J = 6.8 Hz, 12 H). ¹³C NMR data not obtained due to the low solubility of compound 18b. ¹⁹F NMR (DMSO-d ₆, 471 MHz): δ = –78.26.
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

Zusatzmaterial

Supporting Information