Supramolecular gelator based on a [c2]daisy chain rotaxane:efficient gel-solution transition by ring-sliding motion
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摘要
A supramolecular gelator based on the bistable [c2]daisy chain rotaxane is designed and synthesized. The reversible actuation of the [c2]daisy chain renders the formed supramolecular gel with acid/base-responsive switching between gel and monomer solution. The efficient switching process is attributed to the ring-sliding effect of the rotaxane in response to acid/base stimuli.The ring-inhibited hydrogen bonding stacking results in a nearly quantitatively disassembly of the gel network after addition of base which is hard to be realized by traditional heating strategy in hydrogen-bonding-supported gel.
A supramolecular gelator based on the bistable [c2]daisy chain rotaxane is designed and synthesized. The reversible actuation of the [c2]daisy chain renders the formed supramolecular gel with acid/base-responsive switching between gel and monomer solution. The efficient switching process is attributed to the ring-sliding effect of the rotaxane in response to acid/base stimuli.The ring-inhibited hydrogen bonding stacking results in a nearly quantitatively disassembly of the gel network after addition of base which is hard to be realized by traditional heating strategy in hydrogen-bonding-supported gel.
A supramolecular gelator based on the bistable [c2]daisy chain rotaxane is designed and synthesized. The reversible actuation of the [c2]daisy chain renders the formed supramolecular gel with acid/base-responsive switching between gel and monomer solution. The efficient switching process is attributed to the ring-sliding effect of the rotaxane in response to acid/base stimuli.The ring-inhibited hydrogen bonding stacking results in a nearly quantitatively disassembly of the gel network after addition of base which is hard to be realized by traditional heating strategy in hydrogen-bonding-supported gel.
引文
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13(a)Yang S,Luan Z,Gao C,Yu J,Qu D.Sci China Chem,2018,61:306-310;(b)Cui JS,Ba QK,Ke H,Valkonen A,Rissanen K,Jiang W.Angew Chem Int Ed,2018,57:7809-7814;(c)Stoddart JF.Angew Chem Int Ed,2017,56:11094-11125;(d)Zhang ZJ,Zhang HY,Wang H,Liu Y.Angew Chem Int Ed,2011,50:10834-10838;(e)Zhang H,Hu J,Qu DH.Org Lett,2012,14:2334-2337;(f)Cao ZQ,Miao Q,Zhang Q,Li H,Qu DH,Tian H.Chem Commun,2015,51:4973-4976;(g)Gao C,Luan ZL,Zhang Q,Yang S,Rao SJ,Qu DH,Tian H.Org Lett,2017,19:1618-1621
14(a)Dong S,Yuan J,Huang F.Chem Sci,2014,5:247-252;(b)Fu X,Gu RR,Zhang Q,Rao SJ,Zheng XL,Qu DH,Tian H.Polym Chem,2016,7:2166-2170;(c)Zhang Q,Qu DH.Chem Phys Chem,2016,17:1759-1768;(d)Cao ZQ,Luan ZL,Zhang Q,Gu RR,Ren J,Qu DH.Polym Chem,2016,7:1866-1870;(e)Hsueh SY,Kuo CT,Lu TW,Lai CC,Liu YH,Hsu HF,Peng SM,Chen C,Chiu SH.Angew Chem Int Ed,2010,49:9170-9173
15 Goujon A,Lang T,Mariani G,Moulin E,Fuks G,Raya J,Buhler E,Giuseppone N.J Am Chem Soc,2017,139:14825-14828
16(a)Bruns CJ,Stoddart JF.Acc Chem Res,2014,47:2186-2199;(b)Stoddart JF.Chem Soc Rev,2009,38:1802-1820;(c)Chang JC,Tseng SH,Lai CC,Liu YH,Peng SM,Chiu SH.Nat Chem,2017,9:128-134
17(a)Yan X,Xu D,Chi X,Chen J,Dong S,Ding X,Yu Y,Huang F.Adv Mater,2012,24:362-369;(b)Yan X,Xu D,Chen J,Zhang M,Hu B,Yu Y,Huang F.Polym Chem,2013,4:3312-3322;(c)Wang H,Ji X,Li Z,Zhu CN,Yang X,Li T,Wu ZL,Huang F.Mater Chem Front,2017,1:167-171
18(a)Lin HY,Snider BB.J Org Chem,2012,77:4832-4836;(b)Li F,Li Y,Zhou Z,Lv S,Deng Q,Xu X,Yin L.ACS Appl Mater Interfaces,2017,9:23586-23601
19 Coutrot F,Romuald C,Busseron E.Org Lett,2008,10:3741-3744
2(a)Li Z,Zhang YM,Wang HY,Li H,Liu Y.Macromolecules,2017,50:1141-1146;(b)Zhang M,Xu D,Yan X,Chen J,Dong S,Zheng B,Huang F.Angew Chem Int Ed,2012,51:7011-7015;(c)Taylor DL,In Het Panhuis M.Adv Mater,2016,28:9060-9093;(d)Zheng W,Chen LJ,Yang G,Sun B,Wang X,Jiang B,Yin GQ,Zhang L,Li X,Liu M,Chen G,Yang HB.J Am Chem Soc,2016,138:4927-4937
3(a)Ni M,Zhang N,Xia W,Wu X,Yao C,Liu X,Hu XY,Lin C,Wang L.J Am Chem Soc,2016,138:6643-6649;(b)Qiu Y,Park K.Adv Drug Deliver Rev,2012,64:49-60;(c)Ma X,Zhao Y.Chem Rev,2015,115:7794-7839;(d)Wu S,Li J,Liang H,Wang L,Chen X,Jin G,Xu X,Yang HH.Sci China Chem,2017,60:628-634
4(a)Rambarran T,Bertrand A,Gonzaga F,Boisson F,Bernard J,Fleury E,Ganachaud F,Brook MA.Chem Commun,2016,52:6681-6684;(b)Zhang A,Yang L,Lin Y,Yan L,Lu H,Wang L.J Appl Polym Sci,2013,129:2435-2442
5(a)Feng Q,Wei K,Zhang K,Yang B,Tian F,Wang G,Bian L.NPGAsia Mater,2018,10:e455;(b)Guo J,Yuan C,Guo M,Wang L,Yan F.Chem Sci,2014,5:3261-3266;(c)Anderson CA,Jones AR,Briggs EM,Novitsky EJ,Kuykendall DW,Sottos NR,Zimmerman SC.J Am Chem Soc,2013,135:7288-7295
6(a)Hu XY,Zhang P,Wu X,Xia W,Xiao T,Jiang J,Lin C,Wang L.Polym Chem,2012,3:3060-3063b;(b)Zhang Q,Xu TY,Zhao CX,Jin WH,Wang Q,Qu DH.Chem Asian J,2017,12:2549-2553
7(a)Ji X,Zhu K,Yan X,Ma Y,Li J,Hu B,Yu Y,Huang F.Macromol Rapid Commun,2012,33:1197-1202;(b)Wang S,Xu Z,Wang T,Liu X,Lin Y,Shen YZ,Lin C,Wang L.J Photochem Photobiol A-Chem,2018,355:60-66
8(a)Ustinov A,Weissman H,Shirman E,Pinkas I,Zuo X,Rybtchinski B.J Am Chem Soc,2011,133:16201-16211;(b)Obert E,Bellot M,Bouteiller L,Andrioletti F,Lehen-Ferrenbach C,BouéF.J Am Chem Soc,2007,129:15601-15605
9(a)Zhang CW,Ou B,Jiang ST,Yin GQ,Chen LJ,Xu L,Li X,Yang HB.Polym Chem,2018,9:2021-2030;(b)Zhang Q,Wang WZ,Yu JJ,Qu DH,Tian H.Adv Mater,2017,29:1604948;(c)Zhang Q,Qu DH,Wang QC,Tian H.Angew Chem Int Ed,2015,54:15789-15793;(d)Wang WZ,Gao C,Zhang Q,Ye XH,Qu DH.Chem Asian J,2017,12:410-414
10(a)Han Z,Gao Y,Zhai X,Peng J,Tian A,Zhao Y,Hu C.Cryst Growth Des,2016,9:1225-1234;(b)Meazza L,Foster JA,Fucke K,Metrangolo P,Resnati G,Steed JW.Nat Chem,2013,5:42-47;(c)Metrangolo P,Meyer F,Pilati T,Resnati G,Terraneo G.Angew Chem Int Ed,2010,47:6114-6127;(d)Priimagi A,Cavallo G,Metrangolo P,Resnati G.Acc Chem Res,2013,46:2686-2695
11(a)Ji X,Shi B,Wang H,Xia D,Jie K,Wu ZL,Huang F.Adv Mater,2015,27:8062-8066;(b)Hu XY,Wu X,Wang S,Chen D,Xia W,Lin C,Pan Y,Wang L.Polym Chem,2013,4:4292-4297;(c)Zhang Q,Shi CY,Qu DH,Long YT,Feringa BL,Tian H.Sci Adv,2018,4:eaat8192;(d)Wang Q,Zhang YY,Dai XY,Shi XH,Liu WG.Sci China Tech Sci,2017,60:78-83
12(a)Wu X,Yu Y,Gao L,Hu XY,Wang L.Org Chem Front,2016,3:966-970;(b)Folmer BJB,Sijbesma RP,Versteegen RM,van der Rijt JAJ,Meijer EW.Adv Mater,2000,12:874-878;(c)Cordier P,Tournilhac F,Soulié-Ziakovic C,Leibler L.Nature,2008,451:977-980
13(a)Yang S,Luan Z,Gao C,Yu J,Qu D.Sci China Chem,2018,61:306-310;(b)Cui JS,Ba QK,Ke H,Valkonen A,Rissanen K,Jiang W.Angew Chem Int Ed,2018,57:7809-7814;(c)Stoddart JF.Angew Chem Int Ed,2017,56:11094-11125;(d)Zhang ZJ,Zhang HY,Wang H,Liu Y.Angew Chem Int Ed,2011,50:10834-10838;(e)Zhang H,Hu J,Qu DH.Org Lett,2012,14:2334-2337;(f)Cao ZQ,Miao Q,Zhang Q,Li H,Qu DH,Tian H.Chem Commun,2015,51:4973-4976;(g)Gao C,Luan ZL,Zhang Q,Yang S,Rao SJ,Qu DH,Tian H.Org Lett,2017,19:1618-1621
14(a)Dong S,Yuan J,Huang F.Chem Sci,2014,5:247-252;(b)Fu X,Gu RR,Zhang Q,Rao SJ,Zheng XL,Qu DH,Tian H.Polym Chem,2016,7:2166-2170;(c)Zhang Q,Qu DH.Chem Phys Chem,2016,17:1759-1768;(d)Cao ZQ,Luan ZL,Zhang Q,Gu RR,Ren J,Qu DH.Polym Chem,2016,7:1866-1870;(e)Hsueh SY,Kuo CT,Lu TW,Lai CC,Liu YH,Hsu HF,Peng SM,Chen C,Chiu SH.Angew Chem Int Ed,2010,49:9170-9173
15 Goujon A,Lang T,Mariani G,Moulin E,Fuks G,Raya J,Buhler E,Giuseppone N.J Am Chem Soc,2017,139:14825-14828
16(a)Bruns CJ,Stoddart JF.Acc Chem Res,2014,47:2186-2199;(b)Stoddart JF.Chem Soc Rev,2009,38:1802-1820;(c)Chang JC,Tseng SH,Lai CC,Liu YH,Peng SM,Chiu SH.Nat Chem,2017,9:128-134
17(a)Yan X,Xu D,Chi X,Chen J,Dong S,Ding X,Yu Y,Huang F.Adv Mater,2012,24:362-369;(b)Yan X,Xu D,Chen J,Zhang M,Hu B,Yu Y,Huang F.Polym Chem,2013,4:3312-3322;(c)Wang H,Ji X,Li Z,Zhu CN,Yang X,Li T,Wu ZL,Huang F.Mater Chem Front,2017,1:167-171
18(a)Lin HY,Snider BB.J Org Chem,2012,77:4832-4836;(b)Li F,Li Y,Zhou Z,Lv S,Deng Q,Xu X,Yin L.ACS Appl Mater Interfaces,2017,9:23586-23601
19 Coutrot F,Romuald C,Busseron E.Org Lett,2008,10:3741-3744