手性多孔材料在色谱分离分析中的应用
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摘要
手性多孔有机骨架材料(Chiral porous organic frameworks,CPOFs)具有孔性质优异、比表面积高、稳定性好以及易功能化等诸多优点,已经在手性催化、识别和分离等领域中得到应用。手性多孔有机骨架材料主要有手性金属-有机骨架材料(Chiral metal-organic frameworks,CMOFs)和手性共价有机骨架材料(Chiral covalent organic frameworks,CCOFs)及其他材料,这类材料具有特殊的手性识别、吸附作用,在色谱分离分析领域中已成为研究热点之一。该文综述了手性多孔材料的合成及其在色谱分离和选择性吸附中的应用,展望了未来CPOFs材料可能的应用与发展方向。
In recent years,chiral porous organic frameworks(CPOFs) materials have been applied in fields such as chiral catalysis,recognition and separation owing to their outstanding porous properties,high specific surface area,good stability,easy to be functionalized,etc.Chiral porous organic frameworks materials include chiral metal-organic frameworks(CMOFs),chiral covalent organic frameworks(CCOFs) and their composites,which have special chiral recognition and adsorption.These materials have become one of the research hotspots in the field of chromatographic separation and analysis.In this paper,the synthesis of chiral porous materials and their applications in chromatographic separation and selective adsorption are reviewed.The possible applications and development directions of CPOFs materials in future are prospected.
In recent years,chiral porous organic frameworks(CPOFs) materials have been applied in fields such as chiral catalysis,recognition and separation owing to their outstanding porous properties,high specific surface area,good stability,easy to be functionalized,etc.Chiral porous organic frameworks materials include chiral metal-organic frameworks(CMOFs),chiral covalent organic frameworks(CCOFs) and their composites,which have special chiral recognition and adsorption.These materials have become one of the research hotspots in the field of chromatographic separation and analysis.In this paper,the synthesis of chiral porous materials and their applications in chromatographic separation and selective adsorption are reviewed.The possible applications and development directions of CPOFs materials in future are prospected.
引文
[1] Feng X,Liu L L,Honsho Y,Saeki A,Seki S,Irle S,Dong Y P,Nagai A,Jiang D L.Angew.Chem.Int.Ed.,2012,51(11):2618-2622.
[2] Sick T,Hufnagel A G,Kampmann J,Kondofersky I,Calik M,Rotter J A,Doblinger M,Herbert S,Peters K,Bohm D,Knochel P,Medina D D,Fattakhova-Rohlfing D,Bein T.J.Am.Chem.Soc.,2018,140(6):2085-2092.
[3] Wan S,Guo J,Kim J,Ihee H,Jiang D L.Angew.Chem.Int.Ed.,2009,48(30):5439-5442.
[4] Douvali A,Tsipis A C,Eliseeva S V,Petoud S,Papaefstathiou G S,Malliakas C D,Papadas I,Armatas G S,Margiolaki I,Kanatzidis M G,Lazarides T,Manos M J.Angew.Chem.Int.Ed.,2015,54(5):1651-1656.
[5] Yoon M,Srirambalaji R,Kim K.Chem.Rev.,2012,112(2):1196-1231.
[6] Wang X R,Han X,Zhang J,Wu X W,Liu Y,Cui Y.J.Am.Chem.Soc.,2016,138(38):12332-12335.
[7] Pachfule P,Acharjya A,Roeser J,Langenhahn T,Schwarze M,Schomacker R,Thomas A,Schmidt J.J.Am.Chem.Soc.,2018,140(4):1423-1427.
[8] Xu H,Chen X,Gao J,Lin J B,Addicoat M,Irle S,Jiang D L.Chem.Commun.,2014,50(11):1292-1294.
[9] Zhang M D,Dai Q B,Zheng H G,Chen M D,Dai L M.Adv.Mater.,2018,30(10):1705431-1705441.
[10] Zhu J J,Li P Z,Guo W H,Zhao Y L,Zou R Q.Coordin Chem.Rev.,2017,35980-36101.
[11] Fu J R,Das S,Xing G L,Ben T,Valtchev V,Qiu S L.J.Am.Chem.Soc.,2016,138(24):7673-7680.
[12] Gu Z Y,Yang C X,Chang N,Yan X P.Acc.Chem.Res.,2012,45(5):734-745.
[13] Biswal B P,Chaudhari H D,Banerjee R,Kharul U K.Chem.Eur.J.,2016,22(14):4695-4699.
[14] Kang Z X,Peng Y W,Qian Y H,Yuan D Q,Hu Z G,Tee L,Guo Z G,Zhao D.Chem.Mater.,2016,28:1277-1285.
[15] Liu B,Shekhah O,Arslan H K,Liu J X,Woll C,Fischer R A.Angew.Chem.Int.Ed.,2012,51(3):807-810.
[16] Furukawa H,Yaghi O M.J.Am.Chem.Soc.,2009,131:8875–8883.
[17] Vyas V S,Vishwakarma M,Moudrakovski I,Haase F,Savasci G,Ochsenfeld C,Spatz J P,Lotsch B V.Adv.Mater.,2016,28(39):8749-8754.
[18] Tranchemontagne D J,Mendoza-Cortes J L,O'Keeffe M,Yaghi O M.Chem.Soc.Rev.,2009,38(5):1257-1283.
[19] Maurin G,Serre C,Cooper A,Ferey G.Chem.Soc.Rev.,2017,46(11):3104-3107.
[20] Taylor J M,Komatsu T,Dekura S,Otsubo K,Takata M,Kitagawa H.J.Am.Chem.Soc.,2015,137(35):11498-11506.
[21] He H M,Sun Q,Gao W Y,Perman J A,Sun F X,Zhu G S,Aguila B,Forrest K,Space B,Ma S Q.Angew.Chem.Int.Ed.,2018,57(17):4657-4662.
[22] Diercks C S,Yaghi O M.Science,2017,355(6328):923-931.
[23] Biswal B P,Chaudhari H D,Banerjee R,Kharul U K.Chem.Eur.J.,2016,22(14):4695-4699.
[24] Hu Y L,Lian H X,Zhou L J,Li G K.Anal.Chem.,2015,87(1):406-412.
[25] Stegbaue L,Hahn M W,Jentys A,Savasci G,Ochsenfeld C,Lercher J A,Lotsch B V.Chem.Mater.,2015,27:7874-7881.
[26] Luo X,Li G,Hu Y.Talanta,2017,165:377-383.
[27] Nuzhdin A L,Dybtsev D N,Bryliakov K P,Talsi E P,Fedin V P.J.Am.Chem.Soc.,2007,129:12958-12959.
[28] Xie S M,Zhang Z J,Wang Z Y,Yuan L M.J.Am.Chem.Soc.,2011,133(31):11892-11895.
[29] Zhang J H,Xie S M,Chen L,Wang B J,He P G,Yuan L M.Anal.Chem.,2015,87(15):7817-7824.
[30] Qian H L,Yang C X,Yan X P.Nat.Commun.,2016,7:12104-12111.
[31] Zhang M,Pu Z J,Chen X L,Gong X L,Zhu A X,Yuan L M.Chem.Commun.,2013,49(45):5201-5203.
[32] Kuang X,Ma Y,Su H,Zhang J,Dong Y B,Tang B.Anal.Chem.,2014,86(2):1277-1281.
[33] Zhang K,Cai S L,Yan Y L,He Z H,Lin H M,Huang X L,Zheng S R,Fan J,Zhang W G.J.Chromatogr.A,2017,1519:100-109.
[34] Han X,Huang J J,Yuan C,Liu Y,Cui Y.J.Am.Chem.Soc.,2018,140(3):892-895.
[35] Dybtsev D N,Nuzhdin A L,Chun H,Bryliakov K P,Talsi E P,Fedin V P,Kim K.Angew.Chem.Int.Ed.,2006,45(6):916-920.
[36] Dybtsev D N,Yutkin M P,Samsonenko D G,Fedin V P,Nuzhdin A L,Bezrukov A A,Bryliakov K P,Talsi E P,Belosludov R V,Mizuseki H,Kawazoe Y,Subbotin O S,Belosludov V R.Chem.Eur.J.,2010,16(34):10348-10356.
[37] Sawada T,Matsumoto A,Fujita M.Angew.Chem.Int.Ed.,2014,53(28):7228-7232.
[38] Chang C L,Qi X Y,Zhang J W,Qiu Y M,Li X J,Wang X,Bai Y,Sun J L,Liu H W.Chem.Commun.,2015,51(17):3566-3569.
[39] Tang B,Zhang J H,Zi M,Chen X X,Yuan L M.Chirality,2016,28(12):778-783.
[40] Navarro-Sanchez J,Argente-Garcia A I,Moliner-Martinez Y,Roca-Sanjuan D,Antypov D,Campins-Falco P,Rosseinsky M J,Marti-Gastaldo C.J.Am.Chem.Soc.,2017,139(12):4294-4297.
[41] Chen L,Reiss P S,Chong S Y,Holden D,Jelfs K E,Hasell T,Little M A,Kewley A,Briggs M E,Stephenson A,Thomas K M,Armstrong J A,Bell J,Busto J,Noel R,Liu J,Strachan D M,Thallapally P K,Cooper A I.Nat.Mater.,2014,13(10):954-960.
[42] Peng Y W,Gong T F,Zhang K,Lin X C,Liu Y,Jiang J W,Cui Y.Nat.Commun.,2014,5:4406.
[43] Xu H,Gao J,Jiang D L.Nat.Chem.,2015,7(11):905-912.
[44] Xu H S,Ding S Y,An W K,Wu H,Wang W.J.Am.Chem.Soc.,2016,138(36):11489-11492.
[2] Sick T,Hufnagel A G,Kampmann J,Kondofersky I,Calik M,Rotter J A,Doblinger M,Herbert S,Peters K,Bohm D,Knochel P,Medina D D,Fattakhova-Rohlfing D,Bein T.J.Am.Chem.Soc.,2018,140(6):2085-2092.
[3] Wan S,Guo J,Kim J,Ihee H,Jiang D L.Angew.Chem.Int.Ed.,2009,48(30):5439-5442.
[4] Douvali A,Tsipis A C,Eliseeva S V,Petoud S,Papaefstathiou G S,Malliakas C D,Papadas I,Armatas G S,Margiolaki I,Kanatzidis M G,Lazarides T,Manos M J.Angew.Chem.Int.Ed.,2015,54(5):1651-1656.
[5] Yoon M,Srirambalaji R,Kim K.Chem.Rev.,2012,112(2):1196-1231.
[6] Wang X R,Han X,Zhang J,Wu X W,Liu Y,Cui Y.J.Am.Chem.Soc.,2016,138(38):12332-12335.
[7] Pachfule P,Acharjya A,Roeser J,Langenhahn T,Schwarze M,Schomacker R,Thomas A,Schmidt J.J.Am.Chem.Soc.,2018,140(4):1423-1427.
[8] Xu H,Chen X,Gao J,Lin J B,Addicoat M,Irle S,Jiang D L.Chem.Commun.,2014,50(11):1292-1294.
[9] Zhang M D,Dai Q B,Zheng H G,Chen M D,Dai L M.Adv.Mater.,2018,30(10):1705431-1705441.
[10] Zhu J J,Li P Z,Guo W H,Zhao Y L,Zou R Q.Coordin Chem.Rev.,2017,35980-36101.
[11] Fu J R,Das S,Xing G L,Ben T,Valtchev V,Qiu S L.J.Am.Chem.Soc.,2016,138(24):7673-7680.
[12] Gu Z Y,Yang C X,Chang N,Yan X P.Acc.Chem.Res.,2012,45(5):734-745.
[13] Biswal B P,Chaudhari H D,Banerjee R,Kharul U K.Chem.Eur.J.,2016,22(14):4695-4699.
[14] Kang Z X,Peng Y W,Qian Y H,Yuan D Q,Hu Z G,Tee L,Guo Z G,Zhao D.Chem.Mater.,2016,28:1277-1285.
[15] Liu B,Shekhah O,Arslan H K,Liu J X,Woll C,Fischer R A.Angew.Chem.Int.Ed.,2012,51(3):807-810.
[16] Furukawa H,Yaghi O M.J.Am.Chem.Soc.,2009,131:8875–8883.
[17] Vyas V S,Vishwakarma M,Moudrakovski I,Haase F,Savasci G,Ochsenfeld C,Spatz J P,Lotsch B V.Adv.Mater.,2016,28(39):8749-8754.
[18] Tranchemontagne D J,Mendoza-Cortes J L,O'Keeffe M,Yaghi O M.Chem.Soc.Rev.,2009,38(5):1257-1283.
[19] Maurin G,Serre C,Cooper A,Ferey G.Chem.Soc.Rev.,2017,46(11):3104-3107.
[20] Taylor J M,Komatsu T,Dekura S,Otsubo K,Takata M,Kitagawa H.J.Am.Chem.Soc.,2015,137(35):11498-11506.
[21] He H M,Sun Q,Gao W Y,Perman J A,Sun F X,Zhu G S,Aguila B,Forrest K,Space B,Ma S Q.Angew.Chem.Int.Ed.,2018,57(17):4657-4662.
[22] Diercks C S,Yaghi O M.Science,2017,355(6328):923-931.
[23] Biswal B P,Chaudhari H D,Banerjee R,Kharul U K.Chem.Eur.J.,2016,22(14):4695-4699.
[24] Hu Y L,Lian H X,Zhou L J,Li G K.Anal.Chem.,2015,87(1):406-412.
[25] Stegbaue L,Hahn M W,Jentys A,Savasci G,Ochsenfeld C,Lercher J A,Lotsch B V.Chem.Mater.,2015,27:7874-7881.
[26] Luo X,Li G,Hu Y.Talanta,2017,165:377-383.
[27] Nuzhdin A L,Dybtsev D N,Bryliakov K P,Talsi E P,Fedin V P.J.Am.Chem.Soc.,2007,129:12958-12959.
[28] Xie S M,Zhang Z J,Wang Z Y,Yuan L M.J.Am.Chem.Soc.,2011,133(31):11892-11895.
[29] Zhang J H,Xie S M,Chen L,Wang B J,He P G,Yuan L M.Anal.Chem.,2015,87(15):7817-7824.
[30] Qian H L,Yang C X,Yan X P.Nat.Commun.,2016,7:12104-12111.
[31] Zhang M,Pu Z J,Chen X L,Gong X L,Zhu A X,Yuan L M.Chem.Commun.,2013,49(45):5201-5203.
[32] Kuang X,Ma Y,Su H,Zhang J,Dong Y B,Tang B.Anal.Chem.,2014,86(2):1277-1281.
[33] Zhang K,Cai S L,Yan Y L,He Z H,Lin H M,Huang X L,Zheng S R,Fan J,Zhang W G.J.Chromatogr.A,2017,1519:100-109.
[34] Han X,Huang J J,Yuan C,Liu Y,Cui Y.J.Am.Chem.Soc.,2018,140(3):892-895.
[35] Dybtsev D N,Nuzhdin A L,Chun H,Bryliakov K P,Talsi E P,Fedin V P,Kim K.Angew.Chem.Int.Ed.,2006,45(6):916-920.
[36] Dybtsev D N,Yutkin M P,Samsonenko D G,Fedin V P,Nuzhdin A L,Bezrukov A A,Bryliakov K P,Talsi E P,Belosludov R V,Mizuseki H,Kawazoe Y,Subbotin O S,Belosludov V R.Chem.Eur.J.,2010,16(34):10348-10356.
[37] Sawada T,Matsumoto A,Fujita M.Angew.Chem.Int.Ed.,2014,53(28):7228-7232.
[38] Chang C L,Qi X Y,Zhang J W,Qiu Y M,Li X J,Wang X,Bai Y,Sun J L,Liu H W.Chem.Commun.,2015,51(17):3566-3569.
[39] Tang B,Zhang J H,Zi M,Chen X X,Yuan L M.Chirality,2016,28(12):778-783.
[40] Navarro-Sanchez J,Argente-Garcia A I,Moliner-Martinez Y,Roca-Sanjuan D,Antypov D,Campins-Falco P,Rosseinsky M J,Marti-Gastaldo C.J.Am.Chem.Soc.,2017,139(12):4294-4297.
[41] Chen L,Reiss P S,Chong S Y,Holden D,Jelfs K E,Hasell T,Little M A,Kewley A,Briggs M E,Stephenson A,Thomas K M,Armstrong J A,Bell J,Busto J,Noel R,Liu J,Strachan D M,Thallapally P K,Cooper A I.Nat.Mater.,2014,13(10):954-960.
[42] Peng Y W,Gong T F,Zhang K,Lin X C,Liu Y,Jiang J W,Cui Y.Nat.Commun.,2014,5:4406.
[43] Xu H,Gao J,Jiang D L.Nat.Chem.,2015,7(11):905-912.
[44] Xu H S,Ding S Y,An W K,Wu H,Wang W.J.Am.Chem.Soc.,2016,138(36):11489-11492.