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CC BY-NC-ND 4.0 · Organic Materials 2021; 03(02): 374-380
DOI: 10.1055/a-1512-5965
Focus Issue: Supramolecular Optoelectronic Materials
Short Communication

Supramolecular Chirogenesis Engineered by Pt(II)···Pt(II) Metal–Metal Interactions

Chengpeng Wei
a   CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. of China)
,
Mingyang Liu
a   CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. of China)
,
Yifei Han
a   CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. of China)
,
Hua Zhong
a   CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. of China)
,
Feng Wang 
a   CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei, Anhui 230026 (P. R. of China)
› Author Affiliations Funding Information This work was supported by the National Natural Science Foundation of China (21922110 and 21871245), the Fundamental Research Funds for the Central Universities (WK3450000005), and the CAS Youth Innovation Promotion Association (Y201986). The DFT computations were performed at the supercomputing center. We are grateful for the technical support from the High-Performance Computing Center of the University of Science and Technology of China.
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ErrataOrganic Materials 2021; 3(03): e1-e1
DOI: 10.1055/s-0041-1735239

Abstract

Supramolecular chirogenesis represents an effective way to induce chirality at the supramolecular level. For the previous host–guest chirogenic systems, metal–ligand coordination, hydrogen bonding, π–π stacking and hydrophobic interactions have been mainly employed as the non-covalent driving forces. In this study, Pt(II)···Pt(II) metal–metal interactions have been engineered to induce supramolecular chirogenesis, by forming non-covalent clipping structures between chiral platinum receptors and achiral platinum guests together. This results in the emergence of Cotton effects in the metal–metal-to-ligand charge transfer region, ascribed to chirality transfer from trans-1,2-diamide cyclohexane unit on chiral receptors to Pt(II)---Pt(II) non-covalent interacting sites. Supramolecular chirogenesis can be further transferred from organic to aqueous solutions, with higher resistance to concentration and temperature variations in the latter medium. Overall, the current study provides new avenues toward supramolecular chirality systems with tailored properties.

Key words

chirality - host–guest recognition - metallotweezers - Pt(II)–Pt(II) metal–metal interactions - supramolecular chemistry

Supporting Information

Supporting Information for this article is available online at https://doi.org/10.1055/a-1512-5965.


Supporting Information



Publication History

Received: 22 March 2021

Accepted: 16 May 2021

Accepted Manuscript online:
19 May 2021

Article published online:
25 August 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes, or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

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Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

    • 1a Yashima E, Ousaka N, Taura D, Shimomura K, Ikai T, Maeda K. Chem. Rev. 2016; 116: 13752
      CrossrefPubMed
    • 1b Liu M, Zhang L, Wang T. Chem. Rev. 2015; 115: 7304
      CrossrefPubMed
    • 1c Palmans AR. A, Meijer EW. Angew. Chem. Int. Ed. 2007; 46: 8948
      CrossrefPubMed
    • 1d Dorca Y, Greciano EE, Valera JS, Gómez R, Sánchez L. Chem. Eur. J. 2019; 25: 5848
      CrossrefPubMed
    • 2a Borovkov VV, Hembury GA, Inoue Y. Acc. Chem. Res. 2004; 37: 449
      CrossrefPubMed
    • 2b Bobadilla MV. E, Kleij AW. Chem. Sci. 2012; 3: 2421
      CrossrefPubMed
    • 2c Dhamija A, Mondal P, Saha B. Dalton Trans. 2020; 49: 10679
      CrossrefPubMed
  • 3 Borovkov VV, Lintuluoto JM, Inoue Y. J. Am. Chem. Soc. 2001; 123: 2979
    CrossrefPubMed
    • 4a Brahma S, Ikbal SA, Dey S, Rath SP. Chem. Commun. 2012; 48: 4070
      CrossrefPubMed
    • 4b Brahma S, Ikbal SA, Rath SP. Inorg. Chem. 2014; 53: 49
      CrossrefPubMed
    • 4c Ikbal SA, Brahma S, Rath SP. Chem. Commun. 2015; 51: 895
      CrossrefPubMed
    • 5a Wang LL, Chen Z, Liu WE, Ke H, Wang SH, Jiang W. J. Am. Chem. Soc. 2017; 139: 8436
      CrossrefPubMed
    • 5b Zhu H, Li Q, Gao Z, Wang H, Shi B, Wu Y, Shangguan L, Hong X, Wang F, Huang F. Angew. Chem. Int. Ed. 2020; 59: 10868
      CrossrefPubMed
    • 5c Chai H, Chen Z, Wang S.-H, Quan M, Yang L.-P, Ke H, Jian W. CCS Chem. 2020; 2: 440
      CrossrefPubMed
    • 6a Rizzuto FJ, Pröhm P, Plajer AJ, Greenfield JL, Nitschke JR. J. Am. Chem. Soc. 2019; 141: 1707
      CrossrefPubMed
    • 6b Li B, Zheng B, Zhang W, Zhang D, Yang XJ, Wu B. J. Am. Chem. Soc. 2020; 142: 6304
      CrossrefPubMed
    • 7a Korevaar PA, George SJ, Markvoort AJ, Smulders MM, Hilbers PA. J, Schenning AP. H. J, De Greef TF, Meijer EW. Nature 2012; 481: 492
      CrossrefPubMed
    • 7b Dolain C, Jiang H, Léger JM, Guionneau P, Huc I. J. Am. Chem. Soc. 2005; 127: 12943
      CrossrefPubMed
    • 7c George SJ, Tomović Z, Smulders MM. J, de Greef TF. A, Leclère PE. L. G, Meijer EW, Schenning AP. H. J. Angew. Chem. Int. Ed. 2007; 46: 8206
      CrossrefPubMed
    • 8a Greenfield JL, Evans EW, Di Nuzzo D, Di Antonio M, Friend RH, Nitschke JR. J. Am. Chem. Soc. 2018; 140: 10344
      CrossrefPubMed
    • 8b Ishikawa M, Maeda K, Yashima E. J. Am. Chem. Soc. 2002; 124: 7448
      CrossrefPubMed
    • 8c Yashima E, Maeda K, Furusho Y. Acc. Chem. Res. 2008; 41: 1166
      CrossrefPubMed
    • 9a Mauro M, Aliprandi A, Septiadi D, Kehr NS, De Cola L. Chem. Soc. Rev. 2014; 43: 4144
      CrossrefPubMed
    • 9b Yoshida M, Kato M. Coord. Chem. Rev. 2020; 408: 213194
      CrossrefPubMed
    • 9c Herkert L, Sampedro A, Fernández G. CrystEngComm 2016; 18: 8813
      CrossrefPubMed
    • 9d Yam VW.-W, Au VK.-M, Leung SY.-L. Chem. Rev. 2015; 115: 7589
      CrossrefPubMed
    • 9e Crowley JD, Steele IM, Bosnich B. Inorg. Chem. 2005; 44: 2989
      CrossrefPubMed
    • 9f Crowley JD, Steele IM, Bosnich B. Eur. J. Inorg. Chem. 2005; 3907
      PubMed
    • 10a Wong KM.-C, Yam VW.-W. Acc. Chem. Res. 2011; 44: 424
      CrossrefPubMed
    • 10b Gao Z, Han Y, Gao Z, Wang F. Acc. Chem. Res. 2018; 51: 2719
      CrossrefPubMed
    • 10c Han Y, Gao Z, Wang C, Zhong R, Wang F. Coord. Chem. Rev. 2020; 414: 213300
      CrossrefPubMed
    • 11a Chung CY.-S, Yam VW.-W. J. Am. Chem. Soc. 2011; 133: 18775
      CrossrefPubMed
    • 11b Wong KM.-C, Chan MM.-Y, Yam VW.-W. Adv. Mater. 2014; 26: 5558
      CrossrefPubMed
    • 11c Chung CY.-S, Chan KH, Yam VW.-W. Chem. Commun. 2011; 47: 2000
      CrossrefPubMed
    • 11d Chung CY.-S, Yam VW.-W. Chem. Sci. 2013; 4: 377
      CrossrefPubMed
    • 11e Chan MC.-L, Yam VW.-W. Chem. Eur. J. 2011; 17: 11987
      CrossrefPubMed
    • 12a Ly KT, Cheng RW. C, Lin HW, Shiau YJ, Liu SH, Chou PT, Tsao CS, Huang YC, Chi Y. Nat. Photonics 2017; 11: 63
      CrossrefPubMed
    • 12b Chen WC, Sukpattanacharoen C, Chan WH, Huang CC, Hsu HF, Shen D, Hung WY, Kungwan N, Escudero D, Lee CS, Chi Y. Adv. Funct. Mater. 2020; 30: 2002494
      CrossrefPubMed
    • 13a Liu M, Han Y, Zhong H, Zhang X, Wang F. Angew. Chem. Int. Ed. 2021; 60: 3498
      CrossrefPubMed
    • 13b Li Z, Han Y, Nie F, Liu M, Zhong H, Wang F. Angew. Chem. Int. Ed. 2021; 60: 8212
      CrossrefPubMed
    • 13c Tian Y.-K, Shi Y.-G, Yang Z.-S, Wang F. Angew. Chem. Int. Ed. 2014; 53: 6090
      CrossrefPubMed
    • 13d Tian Y.-K, Han Y.-F, Yang Z.-S, Wang F. Macromolecules 2016; 49: 6455
      CrossrefPubMed
    • 13e Zhang X, Han Y, Liu G, Wang F. Chin. Chem. Lett. 2019; 30: 1927
      CrossrefPubMed
  • 14 Synthetic procedure for compound ( SS )-1: Compound (SS)-5 (30.0 mg, 0.08 mmol), [Pt(tpy)Cl](BF4) (128 mg, 0.18 mmol), CuI (20.0 mg, 0.10 mmol) and TEA (3 mL) in DMF were stirred under a nitrogen atmosphere at room temperature for 48 hours. The mixture was evaporated under reduced pressure, and the residue was extracted with H2O/CH2Cl2. The combined organic extracts were removed with a rotary evaporator, and the residue was purified by flash column chromatography (CH2Cl2/CH3OH, 50:1 v/v as the eluent; R f = 0.3) to afford (SS)-1 as a yellow solid (120 mg, 86%). 1H NMR (400 MHz, CDCl3 δ: 9.09 (d, J = 6.0 Hz, 4 H), 8.86 (s, 4 H), 8.75 (d, J = 2.1 Hz, 4 H), 7.76–7.69 (m, 4 H), 7.60 (dd, J = 6.1, 2.1 Hz, 4 H), 7.53–7.46 (m, 4 H), 6.91 (s, 2 H), 4.05 (s, 2 H), 2.26 (d, J = 9.6 Hz, 2 H), 1.88 (s, 2 H), 1.66 (s, 18 H), 1.51 (s, 36 H). 13C NMR (101 MHz, CDCl3:CH3OD = 3:1) δ: 167.4, 166.3, 157.6, 152.8, 152.6, 130.9, 130.8, 130.1, 127.8, 126.0, 124.5, 122.6, 121.0, 51.7, 36.7, 35.6, 30.5, 29.8, 29.3, 28.7. HRMS: m/z: [M – 2BF4]2+, experimental, 780.3229; calculated, 780.3241, error 1.5 ppm
    PubMed
  • 15 Synthetic procedure for compound ( RR )-1: A similar procedure to that of (SS)-1 was adopted, by employing (RR)-5 (250 mg, 2.19 mmol) instead of (SS)-5. Compound (RR)-1 was obtained as a yellow solid (117 mg, 84%). 1H NMR (400 MHz, CDCl3 δ: 9.09 (d, J = 6.0 Hz, 4 H), 8.68 (s, 4 H), 8.59 (s, 4 H), 7.73 (d, J = 7.9 Hz, 4 H), 7.62 (d, J = 6.0 Hz, 4 H), 7.49 (d, J = 8.0 Hz, 4 H), 6.96–6.88 (m, 2 H), 4.06 (s, 2 H), 2.24 (s, 2 H), 1.88 (s, 2 H), 1.66 (s, 18 H), 1.51 (s, 36 H), 1.47 (s, 4 H). 13C NMR (101 MHz, CDCl3 δ: 166.4, 152.7, 130.8, 126.0, 124.2, 121.4, 53.9, 36.8, 35.6, 29.8, 29.3, 28.3, 28.3. HRMS: m/z: [M – 2BF4]2+, experimental, 780.3226; calculated, 780.3241, error 1.9 ppm
    PubMed
    • 16a Tanaka Y, Wong KM.-C, Yam VW.-W. Chem. Sci. 2012; 3: 1185
      CrossrefPubMed
    • 16b Li Z, Han Y, Jin F, Gao Z, Gao Z, Ao L, Wang F. Dalton Trans. 2016; 45: 17290
      CrossrefPubMed
    • 16c Li Z, Han Y, Gao Z, Fu T, Wang F. Mater. Chem. Front. 2018; 2: 76
      CrossrefPubMed
    • 16d Han Y, Tian Y, Li Z, Wang F. Chem. Soc. Rev. 2018; 47: 5165
      CrossrefPubMed
    • 16e Ibáñez S, Poyatos M, Peris E. Angew. Chem. Int. Ed. 2017; 56: 9786
      CrossrefPubMed
    • 16f Biz C, Ibáñez S, Poyatos M, Gusev D, Peris E. Chem. Eur. J. 2017; 23: 14439
      CrossrefPubMed
    • 16g Ibáñez S, Poyatos M, Peris E. Angew. Chem. Int. Ed. 2018; 57: 16816
      CrossrefPubMed
    • 16h Ibáñez S, Peris E. Chem. Eur. J. 2019; 25: 8254
      CrossrefPubMed
    • 17a Leung SY.-L, Tam AY.-Y, Tao C.-H, Chow HS, Yam VW.-W. J. Am. Chem. Soc. 2012; 134: 1047
      CrossrefPubMed
    • 17b Li Z, Han Y, Gao Z, Wang F. ACS Catal. 2017; 7: 4676
      CrossrefPubMed
    • 18a Narayan B, Bejagam KK, Balasubramanian S, George SJ. Angew. Chem. Int. Ed. 2015; 54: 13053
      CrossrefPubMed
    • 18b Sarkar S, Narayan B, George SJ. ChemNanoMat 2020; 6: 1169
      CrossrefPubMed
  • 19 Chen Z, Lohr A, Saha-Möller CR, Würthner F. Chem. Soc. Rev. 2009; 38: 564
    CrossrefPubMed
    • 20a Leung SY.-L, Lam WH, Yam VW.-W. Proc. Natl. Acad. Sci. U.S.A. 2013; 110: 7986
      CrossrefPubMed
    • 20b Norel L, Rudolph M, Vanthuyne N, Williams JA. G, Lescop C, Roussel C, Autschbach J, Crassous J, Réau R. Angew. Chem. Int. Ed. 2010; 49: 99
      CrossrefPubMed
    • 20c Aliprandi A, Croisetu CM, Mauro M, Cola L. Chem. Eur. J. 2017; 23: 5957
      CrossrefPubMed
    • 20d Gao Z, Tian Y, Hsu HK, Han Y, Chan YT, Wang F. CCS Chem. 2021; 3: 105
      CrossrefPubMed