一种基于21-冠-7和柱[5]芳烃分子识别的超分子聚合物

李明阳; 韩康; 李健; 贾学顺; 李春举

doi:10.11777/j.issn1000-3304.2017.16276

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一种基于21-冠-7和柱[5]芳烃分子识别的超分子聚合物

研究论文 | 更新时间：2021-03-12

- 一种基于21-冠-7和柱[5]芳烃分子识别的超分子聚合物
- A Linear Supramolecular Polymer Based on Molecular Recognition of 21-Crown-7 and Pillar[5]arene
- 高分子学报 2017年第1期页码：129-134
- 作者机构：
  
  上海大学化学系上海 200444
- 作者简介：
  
  E-mail: cjli@shu.edu.cn Chun-ju Li, E-mail:cjli@shu.edu.cn
- 基金信息：
  
  国家自然科学基金资助项目(基金号21272155，21472122)
- DOI：10.11777/j.issn1000-3304.2017.16276
  中图分类号：
- 纸质出版日期：2017-1，
  
  收稿日期：2016-9-6，
  
  修回日期：2016-9-25，
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李明阳, 韩康, 李健, 贾学顺, 李春举. 一种基于21-冠-7和柱[5]芳烃分子识别的超分子聚合物[J]. 高分子学报, 2017,(1):129-134.

Li Ming-yang, Han Kang, Li Jian, Jia Xue-shun, Li Chun-ju. A Linear Supramolecular Polymer Based on Molecular Recognition of 21-Crown-7 and Pillar[5]arene[J]. Acta Polymerica Sinica, 2017,(1):129-134.
李明阳, 韩康, 李健, 贾学顺, 李春举. 一种基于21-冠-7和柱[5]芳烃分子识别的超分子聚合物[J]. 高分子学报, 2017,(1):129-134. DOI： 10.11777/j.issn1000-3304.2017.16276.

Li Ming-yang, Han Kang, Li Jian, Jia Xue-shun, Li Chun-ju. A Linear Supramolecular Polymer Based on Molecular Recognition of 21-Crown-7 and Pillar[5]arene[J]. Acta Polymerica Sinica, 2017,(1):129-134. DOI： 10.11777/j.issn1000-3304.2017.16276.

摘要

合成了一个苯并21-冠-7-柱[5]芳烃杂二主题主体分子（

），二级铵盐是21-冠-7大环的合适客体，而柱[5]芳烃空腔可以强络合中性客体基元5-（1H-1，2，3-triazol-1-yl）pentanenitrile（TAPN），因此选择含有2个TAPN的客体

和含有2个二级铵盐的客体

作为连接体，依靠二级铵盐⊂21-冠-7和中性客体⊂柱[5]芳烃正交主客体作用，构筑了一个三组分超分子聚合物（

1，2

和

的摩尔比为1：0.5：0.5），该组装体的形成得到了

H-NMR、DOSY、黏度和SEM等手段的表征.所构筑的超分子聚集体是浓度依赖的，其形成超分子聚合物的临界浓度为49 mmol/L.

Abstract

A heteroditopic host molecule (

) containing a benzo-21-crown-7 and a pillar[5]arene unit was synthesized through the nucleophilic substitution reaction between 4'-chloromethyl benzo-21-crown-7 with monohydroxyl pillar[5]

arene using K

as the base. It is well documented that secondary ammonium salts are suitable guest moieties for 21-crown-7 macrocycle

and pillar[5]arene cavity can strongly bind with neutral guest 5-(1H-1

3-triazol-1-yl) pentanenitrile (TAPN). Therefore

guest

containing two TAPN moieties and guest

containing two secondary ammonium salt binding sites are chosen as the connectors. Based on orthogonal host-guest interactions of secondary ammonium salt⊂benzo-21-crown-7 and neutral guest⊂pillar[5]arene

a three-component supramolecular polymer of

and

(1:0.5:0.5

molar ratio) was constructed

which was characterized by various techniques such as

H-NMR

DOSY

viscosity and SEM. In the concentration-dependent

H-NMR spectra

slow exchange on the NMR timescale was observed for the three-component mixture. At low concentrations

uncomplexed signals of dUC could be obviously found; and at high concentrations

uncomplexed signals were not observed

while the complexed species became very obvious (a

and f

). These results indicated the efficient host-guest interactions in the system. From double-logarithmic curves of specific viscosity (versus monomer concentrations)

the slope of the curve in the low concentration region is close to one

suggesting the formation of small oligomers. At high concentrations

the slope value exceeds to 1.53

revealing the formation of supramolecular polymers with large volumn. The critical polymerization concentration (CPC) is 49 mol/L. DOSY further demonstrates the concentration-dependent assembly of supramolecular aggregates. The measured weight average diffusion coefficient decreased dramatically from 3.24×10

-10

/s to 7.64×10

-11

as the monomer concentration increased. In addition

long and thin fibers with a diameter of approximately 0.8 μm could easily be drawn from a highly concentrated solution of

and

providing further direct evidence for the fabrication of high-molecular-weight supramolecular polymer.

关键词

超分子聚合物自组装冠醚柱芳烃

Keywords

Suparmolecular polymerSelf-assemblyCrown etherPillararene

references

T Aida , E W Meijer , S I Stupp . Science , 2012 . 335 813 - 817 . DOI:10.1126/science.1205962http://doi.org/10.1126/science.1205962.

S L Li , T Xiao , C Lin , L Wang . Chem Soc Rev , 2012 . 41 5950 - 5968 . DOI:10.1039/c2cs35099hhttp://doi.org/10.1039/c2cs35099h.

J M Lehn . Polym Int , 2002 . 51 825 - 839 . DOI:10.1002/(ISSN)1097-0126http://doi.org/10.1002/(ISSN)1097-0126.

P R Ashton , B Odell , M V Reddington , A M Z Slawin , J F Stoddart , D J Williams . Angew Chem Int Ed , 1988 . 27 1550 - 1553 . DOI:10.1002/(ISSN)1521-3773http://doi.org/10.1002/(ISSN)1521-3773.

C F Chen . Chem Commun , 2011 . 47 1674 - 1688 . DOI:10.1039/c0cc04852fhttp://doi.org/10.1039/c0cc04852f.

W Jiang , H D F Winkler , C A Schalley . J Am Chem Soc , 2008 . 130 13852 - 13853 . DOI:10.1021/ja806009dhttp://doi.org/10.1021/ja806009d.

Q Li , W Zhang , O Š Miljanić , C H Sue , C Knobler , Y L Zhao , L Liu , J F Stoddart , O M Yaghi . Science , 2009 . 325 855 - 859 . DOI:10.1126/science.1175441http://doi.org/10.1126/science.1175441.

M Zhang , X Yan , F Huang , Z Niu , H W Gibson . Acc Chem Res , 2014 . 47 1995 - 2005 . DOI:10.1021/ar500046rhttp://doi.org/10.1021/ar500046r.

X Yan , D Xu , J Chen , M Zhang , B Hu , Y Yu , F Huang . Polym Chem , 2013 . 4 3312 - 3322 . DOI:10.1039/c3py00283ghttp://doi.org/10.1039/c3py00283g.

Q H Guo , Z D Fu , L Zhao , M X Wang . Angew Chem Int Ed , 2014 . 53 13548 - 13552 . DOI:10.1002/anie.201407670http://doi.org/10.1002/anie.201407670.

H Chen , J Fan , X Hu , J Ma , S Wang , J Li , Y Yu , X Jia , C Li . Chem Sci , 2015 . 6 197 - 202 . DOI:10.1039/C4SC02422Bhttp://doi.org/10.1039/C4SC02422B.

G W Zhang , P F Li , Z Meng , H X Wang , Y Han , C F Chen . Angew Chem Int Ed , 2016 . DOI:10.1002/anie.201600911http://doi.org/10.1002/anie.201600911 .

D S Guo , Y Liu . Acc Chem Res , 2014 . 47 1925 - 1934 . DOI:10.1021/ar500009ghttp://doi.org/10.1021/ar500009g.

A Harada , Y Takashima , H Yamaguchi . Chem Soc Rev , 2009 . 38 875 - 882 . DOI:10.1039/b705458khttp://doi.org/10.1039/b705458k.

Y Chen , Y Liu . Chem Soc Rev , 2010 . 39 495 - 505 . DOI:10.1039/B816354Phttp://doi.org/10.1039/B816354P.

D H Qu , Q C Wang , Q W Zhang , X Ma , H Tian . Chem Rev , 2015 . 115 7543 - 7588 . DOI:10.1021/cr5006342http://doi.org/10.1021/cr5006342.

Y Liu , Y Yu , J Gao , Z Wang , X Zhang . Angew Chem Int Ed , 2010 . 49 6576 - 6579 . DOI:10.1002/anie.201002415http://doi.org/10.1002/anie.201002415.

Z Huang , L Yang , Y Liu , Z Wang , O A Scherman , X Zhang . Angew Chem Int Ed , 2014 . 53 5351 - 5355 . DOI:10.1002/anie.v53.21http://doi.org/10.1002/anie.v53.21.

L Yang , X Tan , Z Wang , X Zhang . Chem Rev , 2015 . 115 7196 - 7239 . DOI:10.1021/cr500633bhttp://doi.org/10.1021/cr500633b.

U Rauwald , O A Scherman . Angew Chem Int Ed , 2008 . 47 3950 - 3953 . DOI:10.1002/anie.v47:21http://doi.org/10.1002/anie.v47:21.

H Y Gong , B M Rambo , E Karnas , V M Lynch , J L Sessler . Nat Chem , 2010 . 2 406 - 409 . DOI:10.1038/nchem.597http://doi.org/10.1038/nchem.597.

K Jie , Y Zhou , Y Yao , B Shi , F Huang . J Am Chem Soc , 2015 . 137 10472 - 10475 . DOI:10.1021/jacs.5b05960http://doi.org/10.1021/jacs.5b05960.

H Li , X Fan , M Qi , Z Yang , H Zhang , W Tian . Chem Eur J , 2016 . 22 101 - 105 . DOI:10.1002/chem.201504012http://doi.org/10.1002/chem.201504012.

W Zhang , Y M Zhang , S H Li , Y L Cui , J Yu , Y Liu . Angew Chem Int Ed , 2016 . DOI:10.1002/anie.201605420http://doi.org/10.1002/anie.201605420 .

P Wei , X Yan , F Huang . Chem Soc Rev , 2015 . 44 815 - 832 . DOI:10.1039/C4CS00327Fhttp://doi.org/10.1039/C4CS00327F.

T Aida , E Meijer , W , S I Stupp . Science , 2012 . 335 813 - 817 . DOI:10.1126/science.1205962http://doi.org/10.1126/science.1205962.

A Harada , R Kobayashi , Y Takashima , A Hashidzume , H Yamaguchi . Nat Chem , 2011 . 3 34 - 37 . DOI:10.1038/nchem.893http://doi.org/10.1038/nchem.893.

H Yamaguchi , Y Kobayashi , R Kobayashi , Y Takashima , A Hashidzume , A Harada . Nat Commun , 2011 . 3 19596 - 19600.

K P Wang , D S Guo , H X Zhao , Y Liu . Chem Eur J , 2014 . 20 4023 - 4031 . DOI:10.1002/chem.201303344http://doi.org/10.1002/chem.201303344.

D S Guo , T X Zhang , Y X Wang , Y Liu . Chem Commun , 2013 . 49 6779 - 6781 . DOI:10.1039/c3cc41918ehttp://doi.org/10.1039/c3cc41918e.

T Ogoshi , S Kanai , S Fujinami , T Yamagishi , Y Nakamoto . J Am Chem Soc , 2008 . 130 5022 - 5023 . DOI:10.1021/ja711260mhttp://doi.org/10.1021/ja711260m.

M Xue , Y Yang , X Chi , Z Zhang , F Huang . Acc Chem Res , 2012 . 45 1294 - 1308 . DOI:10.1021/ar2003418http://doi.org/10.1021/ar2003418.

C Li . Chem Commun , 2014 . 50 12420 - 12433 . DOI:10.1039/C4CC03170Ahttp://doi.org/10.1039/C4CC03170A.

D Cao , Y Kou , J Liang , Z Chen , L Wang , H Meier . Angew Chem Int Ed , 2009 . 48 9721 - 9723 . DOI:10.1002/anie.200904765http://doi.org/10.1002/anie.200904765.

Y Wang , G Ping , C Li . Chem Commun , 2016 . 52 9858 - 9872 . DOI:10.1039/C6CC03999Ehttp://doi.org/10.1039/C6CC03999E.

T Ogoshi , S Takashima , T Yamagishi . J Am Chem Soc , 2015 . 137 10962 - 10964 . DOI:10.1021/jacs.5b07415http://doi.org/10.1021/jacs.5b07415.

Z Y Li , Y Zhang , C W Zhang , L J Chen , C Wang , H Tan , Y Yu , X Li , H B Yang . J Am Chem Soc , 2014 . 126 8577 - 8589.

C Li , Q Xu , J Li , F Yao , X Jia . Org Biomol Chem , 2010 . 8 1568 - 1576 . DOI:10.1039/b920146ghttp://doi.org/10.1039/b920146g.

C Li , L Zhao , J Li , X Ding , S Chen , Q Zhang , Y Yu , X Jia . Chem Commun , 2010 . 46 9016 - 9018 . DOI:10.1039/c0cc03575khttp://doi.org/10.1039/c0cc03575k.

X B Hu , Z X Chen , L Chen , L Zhang , J L Hou , Z T Li . Chem Commun , 2012 . 48 10999 - 11002 . DOI:10.1039/c2cc36027fhttp://doi.org/10.1039/c2cc36027f.

Y Fang , X Yuan , L Wu , Z Peng , W Feng , N Liu , D Xu , S Li , A Sengupta , P K Mohapatra , L Yuan . Chem Commun , 2015 . 51 4263 - 4266 . DOI:10.1039/C4CC09248Ahttp://doi.org/10.1039/C4CC09248A.

Y Sun , F Guo , T Zuo , J Hua , G Diao . Nat Commun , 2016 . DOI:10.1038/ncomms12042http://doi.org/10.1038/ncomms12042 .

S H Li , H Y Zhang , X Xu , Y Liu . Nat Commun , 2015 . 6 7590 - 7596 . DOI:10.1038/ncomms8590http://doi.org/10.1038/ncomms8590.

X B Hu , Z Chen , G Tang , J L Hou , Z T Li . J Am Chem Soc , 2012 . 134 8384 - 8387 . DOI:10.1021/ja302292chttp://doi.org/10.1021/ja302292c.

H Zhang , Y Zhao . Chem Eur J , 2013 . 19 16862 - 16879 . DOI:10.1002/chem.v19.50http://doi.org/10.1002/chem.v19.50.

W B Hu , H M Yang , W J Hu , M L Ma , X L Zhao , X Q Mi , Y A Liu , J S Li , B Jiang , K Wen . Chem Commun , 2014 . 50 10460 - 10463 . DOI:10.1039/C4CC01810Ahttp://doi.org/10.1039/C4CC01810A.

S Dong , J Yuan , F Huang . Chem Sci , 2014 . 5 247 - 252 . DOI:10.1039/C3SC52481Ghttp://doi.org/10.1039/C3SC52481G.

K Jie , Y Zhou , Y Yao , B Shi , F Huang . J Am Chem Soc , 2015 . 137 10472 - 10475 . DOI:10.1021/jacs.5b05960http://doi.org/10.1021/jacs.5b05960.

T M N Trinh , I Nierengarten , M Heller , J L Gallani , J F Nierengarten . Chem Eur J , 2015 . 21 8019 - 8022 . DOI:10.1002/chem.201501124http://doi.org/10.1002/chem.201501124.

C Li , S Chen , J Li , K Han , M Xu , B Hu , Y Yu , X Jia . Chem Commun , 2011 . 47 11294 - 11296 . DOI:10.1039/c1cc14829jhttp://doi.org/10.1039/c1cc14829j.

K Han , Y Zhang , J Li , Y Yu , X Jia , C Li . Eur J Org Chem , 2013 . 2057-2060 .

X Shu , J Fan , X Wang , W Chen , X Jia , C Li . Org Biomol Chem , 2012 . 10 3393 - 3397 . DOI:10.1039/c2ob25251ahttp://doi.org/10.1039/c2ob25251a.

X Shu , S Chen , J Li , Z Chen , L Weng , X Jia , C Li . Chem Commun , 2012 . 48 2967 - 2969 . DOI:10.1039/c2cc00153ehttp://doi.org/10.1039/c2cc00153e.

C Li , K Han , J Li , H Zhang , J Ma , X Shu , Z Chen , L Weng , X Jia . Org Lett , 2012 . 14 42 - 45 . DOI:10.1021/ol2027834http://doi.org/10.1021/ol2027834.

X Shu , W Chen , D Hou , Q Meng , R Zheng , C Li . Chem Commun , 2014 . 50 4820 - 4823 . DOI:10.1039/c4cc00800fhttp://doi.org/10.1039/c4cc00800f.

C Li , K Han , J Li , Y Zhang , W Chen , Y Yu , X Jia . Chem Eur J , 2013 . 19 11892 - 11897 . DOI:10.1002/chem.201301022http://doi.org/10.1002/chem.201301022.

L B Meng , D Q Li , S Xiong , X Y Hu , L Wang , G Li . Chem Commun , 2015 . 51 4643 - 4646 . DOI:10.1039/C5CC00398Ahttp://doi.org/10.1039/C5CC00398A.

Q Wang , M Cheng , Y Zhao , L Wu , J Jiang , L Wang , Y Pan . Chem Commun , 2015 . 51 3623 - 3626 . DOI:10.1039/C5CC00130Ghttp://doi.org/10.1039/C5CC00130G.

J F Xu , Y Z Chen , L Z Wu , C H Tung , Q Z Yang . Org Lett , 2013 . 15 6148 - 6151 . DOI:10.1021/ol403015shttp://doi.org/10.1021/ol403015s.

N Song , D X Chen , M C Xia , X L Qiu , K Ma , B Xu , W Tian , Y W Yang . Chem Commun , 2015 . 51 5526 - 5529 . DOI:10.1039/C4CC08205Bhttp://doi.org/10.1039/C4CC08205B.

X Wang , K Han , J Li , X Jia , C Li . Polym Chem , 2013 . 4 3998 - 4003 . DOI:10.1039/c3py00462ghttp://doi.org/10.1039/c3py00462g.

X Wang , H Deng , J Li , K Zheng , X Jia , C Li . Marcromol Rapid Commun , 2013 . 34 1856 - 1862 . DOI:10.1002/marc.v34.23-24http://doi.org/10.1002/marc.v34.23-24.

C Zhang , S Li , J Zhang , K Zhu , N Li , F Huang . Org Lett , 2007 . 9 5553 - 5556 . DOI:10.1021/ol702510chttp://doi.org/10.1021/ol702510c.

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