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Diiron Toluene-3,4-dithiolate Complexes with Tris(3-fluorophenyl)phosphine or Tris(4-trifluoromethylphenyl)phosphine: Synthesis, Spectroscopy, X-Ray Crystal Structures, and Electrochemical Properties

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Abstract

In this paper, two diiron toluene-3,4-dithiolate complexes with tris(3-fluorophenyl)phosphine or tris(4-trifluoromethylphenyl)phosphine have been synthesized and characterized. Treatment of hexacarbonyl complex [Fe2(CO)6{{µ-SC6H3(CH3)S}}] (1) with one equivalent of tris(3-fluorophenyl)phosphine or tris(4-trifluoromethylphenyl)phosphine in the presence of Me3NO·2H2O as the oxidative agent afforded complexes [Fe2(CO)5{{P(3-C6H4F)3}}{{µ-SC6H3(CH3)S}}] (2) and [Fe2(CO)5{{P(4-C6H4CF3)3}}{{µ-SC6H3(CH3)S}}] (3) in 90% and 80% isolated yields, respectively. The new complexes obtained above have been characterized by elemental analysis, IR, NMR spectroscopy, and their structures have been further confirmed by single crystal X-ray diffraction analysis. In addition, electrochemical studies revealed that they can catalyze the reduction of protons to molecular H2 in the presence of a weak acid HOAc.

Graphic Abstract

Two diiron toluene-3,4-dithiolate complexes with tris(3-fluorophenyl)phosphine or tris(4-trifluoromethylphenyl)phosphine have been synthesized by carbonyl substitution and studied by elemental analysis, spectroscopy, X-ray diffraction analysis, and cyclic voltammogram.

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References

  1. Evans DH, Pickett CJ (2003) Chem Soc Rev 32:268

    PubMed  Google Scholar 

  2. Tard C, Pickett CJ (2009) Chem Rev 109:2245

    CAS  PubMed  Google Scholar 

  3. Lubitz W, Ogata H, Rüdiger O, Reijerse E (2014) Chem Rev 114:4081

    CAS  PubMed  Google Scholar 

  4. Rauchfuss TB (2015) Acc Chem Res 48:2107

    CAS  PubMed  PubMed Central  Google Scholar 

  5. Li Y, Rauchfuss TB (2016) Chem Rev 116:7043

    CAS  PubMed  PubMed Central  Google Scholar 

  6. Peters JW, Lanzilotta WN, Lemon BJ, Seefeldt LC (1998) Science 282:1853

    CAS  PubMed  Google Scholar 

  7. Nicolet Y, Piras C, Legrand P, Hatchikian CE, Fontecilla-Camps JC (1999) Structure 7:13

    CAS  PubMed  Google Scholar 

  8. Lawrence JD, Li H, Rauchfuss TB, Bénard M, Rohmer MM (2001) Angew Chem Int Ed 40:1768

    CAS  Google Scholar 

  9. Lawrence JD, Li H, Rauchfuss TB (2001). Chem Commun. https://doi.org/10.1039/B104195A

    Article  Google Scholar 

  10. Gloaguen F, Lawrence JD, Schmidt M, Wilson SR, Rauchfuss TB (2001) J Am Chem Soc 126:12518

    Google Scholar 

  11. Zhao X, Georgakaki IP, Miller ML, Yarbrough JC, Darensbourg MY (2001) J Am Chem Soc 123:9710

    CAS  PubMed  Google Scholar 

  12. Lyon EJ, Georgakaki IP, Reibenspies JH, Darensbourg MY (2001) J Am Chem Soc 123:3268

    CAS  PubMed  Google Scholar 

  13. Lyon EJ, Georgakaki IP, Reibenspies JH, Darensbourg MY (1999) Angew Chem Int Ed 38:3178

    CAS  Google Scholar 

  14. Li H, Rauchfuss TB (2002) J Am Chem Soc 124:726

    CAS  PubMed  Google Scholar 

  15. Song LC, Yang ZY, Bian HZ, Liu Y, Wang HT, Liu XF, Hu QM (2005) Organometallics 24:6126

    CAS  Google Scholar 

  16. Cloirec AL, Best SP, Borg S, Davies SC, Evans DJ, Hughes DL, Pickett CJ (1999). Chem Commun. https://doi.org/10.1039/A906391I

    Article  Google Scholar 

  17. Mejia-Rodriguez R, Chong D, Reibenspies JH, Soriaga MP, Darensbourg MY (2004) J Am Chem Soc 126:12004

    CAS  PubMed  Google Scholar 

  18. Capon JF, Hassnaoui SE, Gloaguen F, Schollhammer P, Talarmin J (2005) Organometallics 24:2020

    CAS  Google Scholar 

  19. Hu MQ, Ma CB, Si YT, Chen CN, Liu QT (2007) J Inorg Biochem 101:1370

    CAS  PubMed  Google Scholar 

  20. Zhao X, Chiang CY, Miller ML, Rampersad MV, Darensbourg MY (2003) J Am Chem Soc 125:518

    CAS  PubMed  Google Scholar 

  21. Winter A, Zsolnai L, Huttner G (1982) Z Naturforsch 37b:1430

    CAS  Google Scholar 

  22. APEX2 (2007) version 2009.7-0. Bruker AXS, Inc., Madison

    Google Scholar 

  23. Sheldrick GM (2001) SADABS: program for absorption correction of area detector frames. Bruker AXS Inc., Madison

    Google Scholar 

  24. Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK, Puschmann H (2009) J Appl Crystallogr 42:339

    CAS  Google Scholar 

  25. Sheldrick GM (2008) Acta Crystallogr A 64:112

    CAS  PubMed  Google Scholar 

  26. Zhao PH, Li XH, Liu YF, Liu YQ (2014) J Coord Chem 67:766

    CAS  Google Scholar 

  27. Lin HM, Mu C, Li A, Liu XF, Li YL, Jiang ZQ, Wu HK (2019) Transit Met Chem 44:491

    CAS  Google Scholar 

  28. Kaur-Ghumaan S, Sreenithya A, Sunoj RB (2015) J Chem Sci 127:557

    CAS  Google Scholar 

  29. Zhao PH, Ma ZY, Hu MY, He J, Wang YZ, Jing XB, Chen HY, Wang Z, Li YL (2018) Organometallics 37:1280

    CAS  Google Scholar 

  30. Ghosh S, Hogarth G, Hollingsworth N, Holt KB, Richards I, Richmond MG, Sanchez BE, Unwin D (2013) Dalton Trans 42:6775

    CAS  PubMed  Google Scholar 

  31. Li QL, Lü S, Zhang RF, Zhao D, Ma CL (2019) Polyhedron 160:255

    CAS  Google Scholar 

  32. Ghosh S, Hollingsworth N, Warren M, Hrovat DA, Richmond MG, Hogarth G (2019) Dalton Trans 48:6051

    CAS  PubMed  Google Scholar 

  33. Li QL, Zhang RF, Ma CL, Lü S, Mu C, Li YL (2020) Appl Organomet Chem 34:e5461

    CAS  Google Scholar 

  34. Hu MY, Zhao PH, Li JR, Gu XL, Jing XB, Liu XF (2020) Appl Organomet Chem 34:e5523

    CAS  Google Scholar 

  35. He J, Deng CL, Li Y, Li YL, Wu Y, Zou LK, Mu C, Luo Q, Xie B, Wei J, Hu JW, Zhao PH, Zheng W (2017) Organometallics 36:1322

    CAS  Google Scholar 

  36. Wang Z, He J, Lü S, Jiang WD, Wu Y, Jiang J, Xie Y, Mu C, Li A, Li YL, Li QL (2019) Appl Organomet Chem 33:e5184

    CAS  Google Scholar 

  37. Chen FY, He J, Yu XY, Wang Z, Mu C, Liu XF, Li YL, Jiang ZQ, Wu HK (2018) Appl Organomet Chem 32:e4549

    Google Scholar 

  38. Hasan MM, Hursthouse MB, Kabir SB, Malik KMA (2001) Polyhedron 20:97

    CAS  Google Scholar 

  39. Li RX, Liu XF, Liu T, Yin YB, Zhou Y, Mei SK, Yan J (2017) Electrochim Acta 237:207

    CAS  Google Scholar 

  40. Zhao PH, Hu MY, Li JR, Ma ZY, Wang YZ, He J, Li YL, Liu XF (2019) Organometallics 38:385

    CAS  Google Scholar 

  41. Ghosh S, Sanchez BE, Richards I, Haque MN, Holt KB, Richmond MG, Hogarth G (2016) J Organomet Chem 812:247

    CAS  Google Scholar 

  42. Lin HM, Li JR, Mu C, Li A, Liu XF, Zhao PH, Li YL, Jiang ZQ, Wu HK (2019) Appl Organomet Chem 33:e5196

    CAS  Google Scholar 

  43. Gloaguen F, Lawrence JD, Rauchfuss TB (2001) J Am Chem Soc 123:9476

    CAS  PubMed  Google Scholar 

  44. Vannucci AK, Wang S, Nichol GS, Lichtenberger DL, Evans DH, Glass RS (2010) Dalton Trans 39:3050

    CAS  PubMed  Google Scholar 

  45. Zaffaroni R, Rauchfuss TB, Gray DL, Gioia LD, Zampella G (2012) J Am Chem Soc 134:19260

    CAS  PubMed  PubMed Central  Google Scholar 

  46. Lü S, Zhang RF, Li QL, He J, Li YL (2018) J Organomet Chem 873:66

    Google Scholar 

  47. Lian M, He J, Yu XY, Mu C, Liu XF, Li YL, Jiang ZQ (2018) J Organomet Chem 870:90

    CAS  Google Scholar 

  48. Hu MY, Yan L, Li JR, Wang YH, Zhao PH, Liu XF (2019) Appl Organomet Chem 33:e4949

    Google Scholar 

Download references

Acknowledgements

This research was supported by Zhejiang Provincial Natural Science Foundation of China under Grant LY19B020002, National Natural Science Foundation of China under Grant 21501124, Science & Technology Department of Sichuan Province under Grant 2018JY0235, Education Department of Sichuan Province under Grant 18ZA0337, and Sichuan University of Science & Engineering under Grant S201910622022.

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Authors and Affiliations

  1. School of Materials and Chemical Engineering, Ningbo University of Technology, Ningbo, 315211, China

    Lin Yan & Xu-Feng Liu

  2. College of Chemistry and Environmental Engineering, Sichuan University of Science and Engineering, Zigong, 643000, China

    Jun Yang & Yu-Long Li

  3. College of Chemical Engineering, Zhejiang University of Technology, Hangzhou, 310014, China

    Xing-Hai Liu

  4. Department of Physics, Key Laboratory of ATMMT Ministry of Education, Zhejiang Sci-Tech University, Hangzhou, 310018, China

    Zhong-Qing Jiang

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  1. Lin Yan
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  2. Jun Yang
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  3. Xu-Feng Liu
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  4. Yu-Long Li
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Correspondence to Xu-Feng Liu.

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Yan, L., Yang, J., Liu, XF. et al. Diiron Toluene-3,4-dithiolate Complexes with Tris(3-fluorophenyl)phosphine or Tris(4-trifluoromethylphenyl)phosphine: Synthesis, Spectroscopy, X-Ray Crystal Structures, and Electrochemical Properties. J Chem Crystallogr 51, 183–190 (2021). https://doi.org/10.1007/s10870-020-00844-3

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