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Fabrication of a Janus Single-layered Covalent Organic Framework
- Acta Polymerica Sinica Vol. 50, Issue 3, Pages: 319-326(2019)
- 作者机构：
1.华南理工大学 华南软物质科学与技术高等研究院 广州 510000
2.广州医科大学药学院 广州 510182
- 作者简介：
- 基金信息：
DOI：10.11777/j.issn1000-3304.2019.18234
CLC：Published：2019-3，
Published Online：29 December 2018，
Received：7 November 2018，
Revised：22 November 2018，
扫 描 看 全 文
Zi-wei Si, Yu-feng Tian, Jing Zhao, Wei Zhang. Fabrication of a Janus Single-layered Covalent Organic Framework. [J]. Acta Polymerica Sinica 50(3):319-326(2019)
Zi-wei Si, Yu-feng Tian, Jing Zhao, Wei Zhang. Fabrication of a Janus Single-layered Covalent Organic Framework. [J]. Acta Polymerica Sinica 50(3):319-326(2019) DOI： 10.11777/j.issn1000-3304.2019.18234.
摘要
以在垂直方向上修饰后的双亲性三聚茚的醛类衍生物作为主要单体，通过与对苯二胺在酸催化条件下于油/水界面进行缩合反应，制备了一类非对称性共价有机框架单分子膜. 经此方法制得的膜的红外光谱显示反应过程中，醛基和胺基的特征峰消失，同时出现了亚胺C＝N键的特征吸收峰，表明原料中绝大部分的醛基和胺基被消耗，转化成亚胺键. 透射电镜照片显示新生成的产物为具有数百纳米尺度的纳米片. 原子力显微镜进一步证实此纳米片为厚度约1 nm的单分子层结构. 通过与水的接触角实验证实，双亲性三聚茚所携带的亲水和疏水链分别位于此共价有机框架单分子膜的两侧，从而赋予了此共价有机框架薄膜2个表面对水滴不同的亲和能力.
Abstract
Breaking the out-of-plane symmetry of 2D materials
which results so-called janus 2D materials
will endow them different physical and chemical properties
and thus will further enrich their applications in different fields. In this work
we designed and fabricated a Janus single-layered covalent organic framework using an amphiphilic planar molecule (truxene)
which having different chians at both sides
as monomer. This amphiphilic truxene derivative is prepared by functionalization at its three active methylene positions with hydrophilic and hydrophobic chains
respectively. Since methylene carbon is a sp
3
carbon
the induced hydrophobic and hydryphilic chains are located perpendicular to the phenyl ring in truxene. After poly-condensation reaction with
p
-phenylenediamine at water/dichlormethane interface
a colorless membrane is formed. Fourier transform infrared spectroscopy (FTIR) spectra of the product indicated the almost complete consumption of the starting materials and the formation of imine bond. Transmission electron microscopy (TEM) images of the resulting membrane show that
the shape of product is a well-defined plate like nano-structure. Further investigation through atomic force microscopy (AFM) measurement confirmed the products from the interface consists of film with ~1 nm in thickness
corresponding to the thickness of a single-layered covalent organic framework. Due to the templating effect of water and oil interface
the hydrophilic and hydrophobic chains are orientated to water and oil phase during the poly-condensation reaction
respectively. After the formation of single layered COF
these chains are fixed at different surfaces of the resulting COF. As a consequence
the obtained COF possesses a single layered structure with two different surfaces
in another word
is a Janus covalent organic framework. Demonstrated by contact angle experiments
two surfaces of this Janus COF show different affinities to water droplets.
关键词
共价有机框架非对称性共价有机框架非对称性二维材料非对称性二维聚合物
Keywords
Covalent organic frameworkJanus single-layered covalent organic frameworkJanus 2D materialJanus 2D polymer
references
Novoselov K S, Geim A K, Morozov S V, Jiang D, Zhang Y, Dubonos S V, Grigorieva I V, Firsov A A . Science , 2004 . 306 666 - 669 . DOI:10.1126/science.1102896http://doi.org/10.1126/science.1102896 .
Wang Q H, Zadeh K K, Kis A, Jonathan N, Strano M S . Nature Nanotechnol , 2012 . 7 699 - 712 . DOI:10.1038/nnano.2012.193http://doi.org/10.1038/nnano.2012.193 .
Novoselov K S, Fal'ko V I, Colombo L, Gellert P R, Schwab M G, Kim K . Nature , 2012 . 490 192 - 200 . DOI:10.1038/nature11458http://doi.org/10.1038/nature11458 .
Balandin A A . Nat Mater , 2011 . 10 569 - 581 . DOI:10.1038/nmat3064http://doi.org/10.1038/nmat3064 .
Rao C N R, Srinivasan N, Vaidhyanathan R . Angew Chem Int Ed , 2004 . 43 1446 - 1496 . DOI:10.1002/(ISSN)1521-3773http://doi.org/10.1002/(ISSN)1521-3773 .
Bonaccorso F, Colombo L, Yu G, Stoller M, Tozzini V, Andrea C, Rodney S, Ruoff, Pellegrini V . Science , 2015 . 6217 ( 2 ): 1246501 .
Huang X, Yin Z Y, Wu S X, Qi X Y, He Q Y, Zhang Q H, Yan Q Y, Boey F, Zhang H . Small , 2011 . 14 1876 - 1902.
Li H, Lu G, Wang Y, Yin Z, Cong C, He Q, Wang L, Ding F, Yu T, Zhang H . Small , 2013 . 9 1974 - 1981 . DOI:10.1002/smll.v9.11http://doi.org/10.1002/smll.v9.11 .
Balendhran S, Walia S, Li Q, Ou J Z, Zhuiykov S, Kaner R B, Sriram S, Bhaskaran M, Kalantar-zadeh K . Adv Funct Mater , 2013 . 23 3952 - 3970 . DOI:10.1002/adfm.v23.32http://doi.org/10.1002/adfm.v23.32 .
Nicolosi V, Chhowalla M, Kanatzidis M G, Strano M S, Coleman J N . Science , 2013 . 340 12264 - 12273.
Lee Y H, Zhang X Q, Zhang W, Chang M T, Lin C T, Chang K D, Yu Y C, Wang T W, Chang C S, Li L J, Lin T W . Adv Mater , 2012 . 24 2320 - 2325 . DOI:10.1002/adma.201104798http://doi.org/10.1002/adma.201104798 .
Shi Y, Li H, Li L J . Chem Soc Rev , 2015 . 44 2744 - 2756 . DOI:10.1039/C4CS00256Chttp://doi.org/10.1039/C4CS00256C .
Feng Q, Mao N, Wu J, Xu H, Wang C, Zhang J, Xie L . ACS Nano , 2015 . 9 7450 - 7455 . DOI:10.1021/acsnano.5b02506http://doi.org/10.1021/acsnano.5b02506 .
Hu D, Xu G, Xing L, Yan X, Wang J, Zheng J, Lu Z, Wang P, Pan X, Jiao L . Angew Chem Int Ed , 2017 . 56 3611 - 3615 . DOI:10.1002/anie.201700439http://doi.org/10.1002/anie.201700439 .
Feng X, Tang Q, Zhou J, Fang J, Ding P, Sun L, Shi L . Cryst Res Technol , 2013 . 48 363 - 368 . DOI:10.1002/crat.201300003http://doi.org/10.1002/crat.201300003 .
Qi H, Wang W D, Li C Y . ACS Macro Lett , 2014 . 3 675 - 678 . DOI:10.1021/mz5002806http://doi.org/10.1021/mz5002806 .
Walther A, Müller A H E . Chem Rev , 2013 . 113 5194 - 5261 . DOI:10.1021/cr300089thttp://doi.org/10.1021/cr300089t .
Wolf A, Walther A, Muller A . Macromolecules , 2011 . 44 9221 - 9229 . DOI:10.1021/ma2020408http://doi.org/10.1021/ma2020408 .
Pfeffermann M, Dong R, Graf R, Zajaczkowski W, Gorelik T, Pisula W, Narita A, Müllen K, Feng X . J Am Chem Soc , 2015 . 137 14525 - 14532 . DOI:10.1021/jacs.5b09638http://doi.org/10.1021/jacs.5b09638 .
Ding S Y, Wang W . Chem Soc Rev , 2013 . 42 548 - 568 . DOI:10.1039/C2CS35072Fhttp://doi.org/10.1039/C2CS35072F .
Feng X, Dinga X S and Jiang D L . Chem Soc Rev , 2012 . 41 6010 - 6022 . DOI:10.1039/c2cs35157ahttp://doi.org/10.1039/c2cs35157a .
Liu X H, Guan C Z, Wang D, Wang L J . Adv Mater , 2014 . 26 6912 - 6920 . DOI:10.1002/adma.v26.40http://doi.org/10.1002/adma.v26.40 .
Díaza H, Corma A . Coord Chem Rev , 2016 . 311 85 - 124 . DOI:10.1016/j.ccr.2015.12.010http://doi.org/10.1016/j.ccr.2015.12.010 .
Mgller V, Hinaut A, Moradi M, Baljozovic M, Jung M A, Shahgaldian P, Mchwald H, Hofer G, Krcger M, King M T, Meyer E, Glatzel T, Schlgter A D . Angew Chem Int Ed , 2018 . 57 10584 - 10588 . DOI:10.1002/anie.201804937http://doi.org/10.1002/anie.201804937 .
Feng X L, Schlgter A D . Angew Chem Int Ed , 2018 . 57 13748 - 13763 . DOI:10.1002/anie.201803456http://doi.org/10.1002/anie.201803456 .
Murray D J, Patterson D D, Payamyar P, Bhola R, Song W, Lackinger M, Schlüter A D, King B T . J Am Chem Soc , 2015 . 137 3450 - 3453 . DOI:10.1021/ja512018jhttp://doi.org/10.1021/ja512018j .
Chen Y G, Li M, Payamyar P, Zheng Z K, Sakamoto J, Schlüter A D . ACS Macro Lett , 2014 . 3 153 - 158 . DOI:10.1021/mz400597khttp://doi.org/10.1021/mz400597k .
Payamyar P, Kaja P, Vargas C R, Stemmer A, Murray D J, Johnson C J, King B T, Schiffmann F, Vondele J V, Renn A, Götzinger S, Ceroni P, Schütz A, Lee L T, Zheng Z, Sakamoto J, Schlüter A D . Adv Mater , 2014 . 26 2052 - 2058 . DOI:10.1002/adma.201304705http://doi.org/10.1002/adma.201304705 .
Wang B B, Li B, Ferrier R C M, Li J C Y . Macromol Rapid Commun , 2010 . 31 169 - 175.
Laird E D, Li C Y . Macromolecules , 2013 . 46 2877 - 2891 . DOI:10.1021/ma400035jhttp://doi.org/10.1021/ma400035j .
Wang B B, Li B, Dong B, Zhao B, Li C Y . Macromolecules , 2010 . 43 9234 - 9238 . DOI:10.1021/ma101772fhttp://doi.org/10.1021/ma101772f .
Wang B B, Li B, Dong B, Zhao B, Li C Y . Polymer , 2010 . 51 4814 - 4822 . DOI:10.1016/j.polymer.2010.08.016http://doi.org/10.1016/j.polymer.2010.08.016 .
Wang B B, Li B, Dong B, Zhao B, Li C Y . J Am Chem Soc , 2008 . 130 11594 - 11595 . DOI:10.1021/ja804192ehttp://doi.org/10.1021/ja804192e .
Li B, Ni L B, Li C Y . Macromolecules , 2008 . 41 149 - 155 . DOI:10.1021/ma702047khttp://doi.org/10.1021/ma702047k .
Li B, Li C Y . J Am Chem Soc , 2007 . 129 12 - 13 . DOI:10.1021/ja0668318http://doi.org/10.1021/ja0668318 .
Zhou T, Wang B B, Dong B, Li C Y . Macromolecules , 2012 . 45 8780 - 8789 . DOI:10.1021/ma3019987http://doi.org/10.1021/ma3019987 .
Deng R H, Liang F X, Zhou P, Zhang C L, Qu X Z, Wang Q, Li J L, Zhu J T, Yang Z Z . Adv Mater , 2014 . 26 4469 - 4472 . DOI:10.1002/adma.v26.26http://doi.org/10.1002/adma.v26.26 .
Liang F X, Shen K, Qu X Z, Zhang C L, Wang Q, Li J L, Liu J G, Yang Z Z . Angew Chem Int Ed , 2011 . 50 2379 - 2382 . DOI:10.1002/anie.201007519http://doi.org/10.1002/anie.201007519 .
Liang F X, Zhang C L, Yang Z Z . Adv Mater , 2014 . 26 6944 - 6949 . DOI:10.1002/adma.v26.40http://doi.org/10.1002/adma.v26.40 .
Yang H L, Liang F X, Wang X, Chen Y, Zhang C L, Wang Q, Qu X Z, Li J L, Wu D C, Yang Z Z . Macromolecules , 2013 . 46 2754 - 2759 . DOI:10.1021/ma400261yhttp://doi.org/10.1021/ma400261y .
Chen Y, Liang F X, Yang H L, Zhang C L, Wang Q, Qu X Z, Li J L, Cai Y L, Qiu D, Yang Z Z . Macromolecules , 2012 . 45, 3 1460 - 1467.
Walther A, Andre X, Drechsler M, Abetz V, Müller A H E . J Am Chem Soc , 2007 . 129 6187 - 6198 . DOI:10.1021/ja068153vhttp://doi.org/10.1021/ja068153v .
Walther A, Go ldel A, Mü ller A H E . Polymer , 2008 . 49 3217 - 3227 . DOI:10.1016/j.polymer.2008.05.023http://doi.org/10.1016/j.polymer.2008.05.023 .
Sperschneider A, Schacher A F H, Tsarkova L, Böker A, Müller A H E . Macromolecules , 2010 . 43 10213 - 10215 . DOI:10.1021/ma102293zhttp://doi.org/10.1021/ma102293z .
Retsch M, Walther A, Loos K, Müller A H E . Langmuir , 2008 . 24 9421 - 9429 . DOI:10.1021/la8009767http://doi.org/10.1021/la8009767 .
Abetz L V, Müller A H E . Macromolecules , 2003 . 36 7894 - 7898 . DOI:10.1021/ma0345551http://doi.org/10.1021/ma0345551 .
Frutos O D, Granier T, Go mez-Lor B, Barbero J J, Monge A, Puebla E G, Echavarren A M . Chem Eur J , 2002 . 8 2879 - 2890 . DOI:10.1002/1521-3765(20020703)8:13<2879::AID-CHEM2879>3.0.CO;2-4http://doi.org/10.1002/1521-3765(20020703)8:13<2879::AID-CHEM2879>3.0.CO;2-4 .
Gadwal I, Sheng G, Thankamony R L, Liu Y, Li H, Lai Z P . ACS Appl Mater Interfaces , 2018 . 10 12295 - 2299 . DOI:10.1021/acsami.7b19450http://doi.org/10.1021/acsami.7b19450 .
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