Thermal- and Light-driven Metathesis Reactions Between Different Diselenides

Abstract

Thermal- and light-driven diselenide metathesis reactions with different types of diselenides are investigated systematically. Their exchange reaction rates and equilibrium conversions are compared in the aspects of the different diselenide structures, activation conditions and solvents. As a result, the metathesis reactions between diselenide small molecules are demonstrated with high dynamic and sensitive features, which can be broadly tuned by varying the electron affinity and aromaticity of the diselenide substituents and external conditions(e.g., solvent, stimulus mode). The current work thus will not only advance our understanding on diselenide metathesis chemistry, but also promote concrete and impactful studies in selenium-containing materials.

Keywords

Dynamic covalent bond / Metathesis / Diselenide

References

[1] Rowan S J, Cantrill S J, Cousins G R L, Sanders J K M, Stoddart J F. Angew. Chem. Int. Ed., 2002, 41: 898.

[2] Corbett P T, Leclaire J, Vial L, West K R, Wietor J L, Sanders J K M, Otto S. Chem. Rev., 200, 106: 3652.

[3] Deng Y K, Yuan Y, Chen Y L. CCS Chem., 2020, 2: 1316.

[4] Zhang X, Xu H P, Dong Z Y, Wang Y P, Liu J Q, Shen J C. J. Am. Chem. Soc., 2004, 126: 10556.

[5] Xia J H, Li T Y, Li C J, Xu H P. Macromolecules, 2018, 51: 7435.

[6] Xia J H, Zhao P, Pan S J, Xu H P. ACS Macro. Lett., 2019, 8: 629.

[7] Cromwell O R, Chung J, Guan Z B. J. Am. Chem. Soc., 2015, 137: 6492.

[8] Belowich M E, Stoddart J F. Chem. Soc. Rev., 2012, 41: 2003.

[9] Ciaccia M, Stefano S D. Org. Biomol. Chem., 2015, 13: 646.

[10] Nishimura Y, Chung J, Muradyan H, Guan Z B. J. Am. Chem. Soc., 2017, 139: 14881.

[11] Otsuka H, Nagano S, Kobashi Y, Maeda T, Takahara A. Chem. Commun., 2010, 46: 1150.

[12] Fortman D J, Snyder R L, Sheppard D T, Dichtel W R. ACS Macro. Lett., 2018, 7: 12261.

[13] Imato K, Nishihara M, Kanehara T, Amamoto Y, Takahara A, Otusuka H. Angew. Chem. Int. Ed., 2012, 51: 1138.

[14] Ying H Z, Zhang Y F, Cheng J J. Nat. Commun., 2014, 5: 3218.

[15] Pan S J, Yang J C, Ji S B, Li T Y, Gao S Q, Sun C X, Xu H P. CCS Chem., 2020, 2: 225.

[16] Delius M V, Geertsema E M, Leigh D A. Nat. Chem., 2010, 2: 96.

[17] Zou W K, Dong J T, Luo Y W, Zhao Q, Xie T. Adv. Mater., 2017, 29: 1606100.

[18] Chen M, Gu Y W, Singh A, Zhong M J, Jordan A M, Biswas S, Korly L T J, Balazs A C, Johnson J A. ACS Cent. Sci., 2017, 3: 124.

[19] Li T Y, Xu H P. Cell Rep. Phys. Sci., 2020, 1: 100111.

[20] Yang J C, Pan S J, Gao S Q, Dai Y H, Xu H P. Biomaterials, 2020, 249: 120054.

[21] Sun C X, Tan Y Z, Xu H P. ACS Materials Lett., 2020, 2: 1173.

[22] Kildahl N K. J. Chem. Educ., 1995, 72: 423.

[23] Ji S B, Cao W, Yu Y, Xu H P. Angew. Chem. Int. Ed., 2014, 53: 6781.

[24] Fan F Q, Ji S B, Sun C X, Liu C, Yu Y, Fu Y, Xu H P. Angew. Chem. Int. Ed., 2018, 57: 16426.

[25] Wu Q, Yuan Y, Chen F Y, Sun C X, Xu H P, Chen Y L. ACS Macro. Lett., 2020, 9: 1547.

[26] Fan F Q, Liu C, Wang S, Lv J Q, Li W Z, Fu Y, Xu H P. J. Mater. Chem. C., 2019, 7: 10777.

[27] Yuan W, Yuan Y, Chen Y L. Acta Polym. Sin., 201, 11: 1495.

[28] Liu C, Xia J H, Ji S B, Fan Z Y, Xu H P. Chem. Commun., 2019, 55: 2813.

[29] Zhou X, Liu H, Mo Z, Ma X, Chen Y, Tang H, Pan Y, Xu Y. Chem. Asian J., 2020, 15: 1536.

[30] Kommula D, Li Q, Ning S, Liu W J, Wang Q, Zhao Z K. Synth. Commun., 2020, 50: 1026.

[31] Singh D, Deobald A M, Camargo L R S, Tabarelli G, Rodrigues O E D, Braga A L. American Chemical Society., 2010, 15: 3288.

[32] Redon S, Kosso A R O, Broggi J, Vanelle P. Synthesis, 2019, 51: 3758.

[33] Ma N, Li Y, Xu H P, Wang Z Q, Zhang X. J. Am. Chem. Soc., 2010, 132: 442.

[34] Banchereau E., Lacomhe S., Ollivier J., Tetrahedron Letters, 1995, 8197

[35] Tankam T, Poochampa K, Vilaivan T, Sukwattanasinitt M, Wacharasindhu S. Tetrahedron, 201, 72: 788.

[36] Caraballo R., Rahm M., Vongvilai P., Brinck T., Ramstrom O., Chem. Commun., 2008, 6603