Triggering a [2]rotaxane molecular shuttle through hydrogen sulfide
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摘要
A novel chemically-controlled [2]rotaxane molecular shuttle was successfully designed and synthesized. A H_2 S-responsive bulk barrier was introduced between the two identical recognition stations of the [2]rotaxane to prevent dynamic shuttling of the macrocycle. Upon addition of H_2 S, the complete intramolecular cascade reaction occurs in a controllable manner, resulting in removal of the bulk barrier and the shuttling motion of the macrocycle between the two stations recovers.
A novel chemically-controlled [2]rotaxane molecular shuttle was successfully designed and synthesized. A H_2 S-responsive bulk barrier was introduced between the two identical recognition stations of the [2]rotaxane to prevent dynamic shuttling of the macrocycle. Upon addition of H_2 S, the complete intramolecular cascade reaction occurs in a controllable manner, resulting in removal of the bulk barrier and the shuttling motion of the macrocycle between the two stations recovers.
A novel chemically-controlled [2]rotaxane molecular shuttle was successfully designed and synthesized. A H_2 S-responsive bulk barrier was introduced between the two identical recognition stations of the [2]rotaxane to prevent dynamic shuttling of the macrocycle. Upon addition of H_2 S, the complete intramolecular cascade reaction occurs in a controllable manner, resulting in removal of the bulk barrier and the shuttling motion of the macrocycle between the two stations recovers.
引文
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3 (a)Collier CP,Mattersteig G,Wong EW,Luo Y,Beverly K,Sampaio J,Raymo FM,Stoddart JF,Heath JR.Science,2000,289:1172–1175;(b)Fujita M.Acc Chem Res,1999,32:53–61;(c)Chen Q,Sun J,Li P,Hod I,Moghadam PZ,Kean ZS,Snurr RQ,Hupp JT,Farha OK,Stoddart JF.J Am Chem Soc,2016,138:14242–14245
4 (a)Koumura N,Zijlstra RWJ,van Delden RA,Harada N,Feringa BL.Nature,1999,401:152–155;(b)Shu W,Liu D,Watari M,Riener CK,Strunz T,Welland ME,Balasubramanian S,McKendry RA.J Am Chem Soc,2005,127:17054–17060;(c)Yu JJ,Cao ZQ,Zhang Q,Yang S,Qu DH,Tian H.Chem Commun,2016,52:12056–12059
5 Kim K.Chem Soc Rev,2002,31:96–107
6 (a)Cao ZQ,Miao Q,Zhang Q,Li H,Qu DH,Tian H.Chem Commun,2015,51:4973–4976;(b)Li H,Qu DH.Sci China Chem,2015,58:916 –921;(c)Liu G,Xu X,Chen Y,Wu X,Wu H,Liu Y.Chem Commun,2016,52:7966–7969
7(a)Jimenez-Molero MC,Dietrich-Buchecker C,Sauvage JP.Chem Commun,2003,14:1613–1616;(b)Liu Y,Flood AH,Bonvallet PA,Vignon SA,Northrop BH,Tseng HR,Jeppesen JO,Huang TJ,Brough B,Baller M,Magonov S,Solares SD,Goddard WA,Ho CM,Stoddart JF.J Am Chem Soc,2005,127:9745–9759;(c)Fu X,Zhang Q,Rao SJ,Qu DH,Tian H.Chem Sci,2016,7:1696–1701
8 (a)Cheng C,McGonigal PR,Schneebeli ST,Li H,Vermeulen NA,Ke C,Stoddart JF.Nat Nanotech,2015,10:547–553;(b)Ragazzon G,Baroncini M,Silvi S,Venturi M,Credi A.Nat Nanotech,2014,10:70 –75
9 Wang X,Tan L,Yang Y.Acta Chim Sin,2016,74:303
10 (a)Li H,Li X,Cao ZQ,Qu DH,ren H,Tian H.ACS Appl Mater Interfaces,2014,6:18921–18929;(b)Meng Z,Xiang JF,Chen CF.J Am Chem Soc,2016,138:5652–5658
11 (a)Li Y,Li H,Li Y,Liu H,Wang S,He X,Wang N,Zhu D.Org Lett,2005,7:4835–4838;(b)Gao C,Luan ZL,Zhang Q,Yang S,Rao SJ,Qu DH,Tian H.Org Lett,2017,19:1618–1621
12 Serreli V,Lee CF,Kay ER,Leigh DA.Nature,2007,445:523–527
13 Alvarez-Pérez M,Goldup SM,Leigh DA,Slawin AMZ.J Am Chem Soc,2008,130:1836–1838
14 BernJ,Alajariń M,Orenes RA.J Am Chem Soc,2010,132:10741–10747
15 Fernandes A,Viterisi A,Aucagne V,Leigh DA,Papot S.Chem Commun,2012,48:2083–2085
16 Li L,Rose P,Moore PK.Annu Rev Pharmacol Toxicol,2011,51:169 –187
17 Yan Q,Sang W.Chem Sci,2016,7:2100–2105
18 Wada T,Ohkubo A,Mochizuki A,Sekine M.Tetrahedron Lett,2001,42 :1069–1072
19 Matsuda H,Hashimoto M,Okuno T.Synth Commun,2002,32:3347–3355
20 Cao X,Lin W,Zheng K,He L.Chem Commun,2012,48:10529–10531