Tetraphenylethene-Based Covalent Organic Frameworks (COFs): Design, Synthesis and Applications

Ziqing Wang; Jinfeng Du; Futai Lu; Qiliang Deng

doi:10.7536/PC230516

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Prog Chem ›› 2024, Vol. 36 ›› Issue (1) : 67-80. DOI: 10.7536/PC230516

Review

Tetraphenylethene-Based Covalent Organic Frameworks (COFs): Design, Synthesis and Applications

Ziqing Wang ¹ ,
Jinfeng Du ² ,
Futai Lu ¹^,²^,^* ,
Qiliang Deng ¹^,²^,^*

Author information +

History +

Abstract

Covalent organic frameworks (COFs) as a new class of crystalline porous materials are assembled by appropriate building blocks through covalent bonds. COFs have been utilized in many fields such as storage and separation of gases, catalysis, proton conduction, energy storage, optoelectronics, sensing and biomedicine due to their regular channels, high thermal stability, high crystallinity and adjustable structure. In recent years, tetraphenylethylene-based covalent organic frameworks (TPE-based COFs) have attracted much attention due to their obvious aggregation induced luminescence effect, simple synthesis and easy functionalization. In this paper, the construction units, topological structures, synthesis strategies and application progress of TPE-based COFs in different fields are briefly reviewed. Finally, the development prospects and possible challenges of TPE-based COFs are pointed out.

Contents

1 Introduction

2 Construction unit and topological structure of TPE-based COFs

3 Synthesis strategy of TPE-based COFs

4 Applications

4.1 Catalysis

4.2 Adsorption

4.2.1 Ions adsorption

4.2.2 Gas adsorption

4.2.3 Biomolecule adsorption

4.3 Sensors

4.3.1 Sensors for detecting explosives

4.3.2 Ion sensors

4.3.3 Acid-base sensors

4.3.4 Enantioselective sensors

4.3.5 Biosensors

4.4 Optoelectronic

4.4.1 Light emitting diode

4.4.2 Electrochemical energy storage

4.4.3 Others

4.5 Bio-related applications

5 Prospects and challenges

Key words

tetraphenylethylene / covalent organic frameworks / building blocks / topology / applications

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Ziqing Wang , Jinfeng Du , Futai Lu , et al. Tetraphenylethene-Based Covalent Organic Frameworks (COFs): Design, Synthesis and Applications[J]. Progress in Chemistry. 2024, 36(1): 67-80 https://doi.org/10.7536/PC230516

References

List( Publishing order | Descend order by publishing year | Descend order by cited within ) Chart analysis

[1]	Luo J D, Xie Z L, Lam J W Y, Cheng L, Tang B Z, Chen H Y, Qiu C F, Kwok H S, Zhan X W, Liu Y Q, Zhu D B. Chem. Commun., 2001, (18): 1740. Cited in this article [1]

[2]	Wen J, Huang Z, Hu S, Li S, Li W Y, Wang X L. J. Hazard. Mater., 2016, 318: 363. Cited in this article [1]

[3]	Selvaraj M, Rajalakshmi K, Ahn D H, Yoon S J, Nam Y S, Lee Y, Xu Y G, Song J W, Lee K B. Anal. Chimica Acta, 2021, 1148: 238178. Cited in this article [1]

[4]	Zhan C, Zhang G X, Zhang D Q. ACS Appl. Mater. Interfaces, 2018, 10(15): 12141. Cited in this article [1]

[5]	Zhang Y Y, Li Y X, Yang N, Yu X, He C H, Niu N, Zhang C Y, Zhou H P, Yu C, Jiang S C. Sens. Actuat. B Chem., 2018, 257: 1143. Cited in this article [1]

[6]	Wang Z Y, Gu Y, Liu J Y, Cheng X, Sun J Z, Qin A J, Tang B Z. J. Mater. Chem. B, 2018, 6(8): 1279. Cited in this article [1]

[7]	Wang Y L, Liu H L, Chen Z, Pu S Z. Spectrochim. Acta A Mol. Biomol. Spectrosc., 2020, 245: 118928. Cited in this article [1]

[8]	Palma-Cando A, Woitassek D, Brunklaus G, Scherf U. Mater. Chem. Front., 2017, 1(6): 1118. Cited in this article [1]

[9]	Lv W X, Yang Q T, Li Q, Li H Y, Li F. Anal. Chem., 2020, 92(17): 11747. Cited in this article [1]

[10]	Lin G W, Peng H R, Chen L, Nie H, Luo W W, Li Y H, Chen S M, Hu R R, Qin A J, Zhao Z J, Tang B Z. ACS Appl. Mater. Interfaces, 2016, 8(26): 16799. Cited in this article [1]

[11]	Liao C W, Hsu Y C, Chu C C, Chang C H, Krucaite G, Volyniuk D, Grazulevicius J V, Grigalevicius S. Org. Electron., 2019, 67: 279. Cited in this article [1]

[12]	Huang C G, Zhou S N, Chen C, Wang X Y, Ding R, Xu Y S, Cheng Z W, Ye Z Q, Sun L J, Wang Z J, Hu D Y, Jia X D, Zhang G Y, Gao S. Small, 2022, 18(47): 2205062. Cited in this article [1]

[13]	Su S, Ma Y F, Tian L M, Wang Z. Sci. Sin. Chimica, 2017, 47(9): 1075. (苏姗, 马宇帆, 田立枚, 王卓. 中国科学: 化学, 2017, 47(9): 1075.). Cited in this article [1]

[14]	Zhang C H, Wu Z T, Xie C X. ShanDong Chem. Ind., 2022, 51(19): 93. ( 张程昊, 吴中涛, 解从霞. 山东化工, 2022, 51(19): 93.). Cited in this article [1]

[15]	Luo Y Q, Feng L, Zheng R L. AnHui Chem Ind, 2022, 48(4): 10. (罗一权, 冯亮, 郑仁林. 安徽化工, 2022, 48(4): 10.). Cited in this article [1]

[16]	Côté A P, Benin A I, Ockwig N W, O'Keeffe M, Matzger A J, Yaghi O M. Science, 2005, 310(5751): 1166. Cited in this article [1]

[17]	Côté A P, El-Kaderi H M, Furukawa H, Hunt J R, Yaghi O M. J. Am. Chem. Soc., 2007, 129(43): 12914. Cited in this article [1]

[18]	Hunt J R, Doonan C J, LeVangie J D, Côté A P, Yaghi O M. J. Am. Chem. Soc., 2008, 130(36): 11872. Cited in this article [1]

[19]	Waller P J, Gándara F, Yaghi O M. Acc. Chem. Res., 2015, 48(12): 3053. Cited in this article [1]

[20]	Rodríguez-San-Miguel D, Zamora F. Chem. Soc. Rev., 2019, 48(16): 4375. Cited in this article [1]

[21]	Liu R Y, Tan T K, Gong Y F, Chen Y Z, Li Z E, Xie S L, He T, Lu Z, Yang H, Jiang D L. Chem. Soc. Rev., 2021, 50(1): 120. Cited in this article [1]

[22]	Geng K Y, He T, Liu R Y, Dalapati S, Tan K T, Li Z P, Tao S S, Gong Y F, Jiang Q H, Jiang D L. Chem. Rev., 2020, 120(16): 8814. Cited in this article [1]

[23]	Guo L L, Yang L, Li M Y, Kuang L J, Song Y H, Wang L. Coord. Chem. Rev., 2021, 440: 213957. Cited in this article [1]

[24]	Meng Z, Mirica K A. Chem. Soc. Rev., 2021, 50(24): 13498. Cited in this article [1]

[25]	Patial S, Soni V, Kumar A, Raizada P, Ahamad T, Pham X M, Van Le Q, Nguyen V H, Thakur S, Singh P. Environ. Res., 2023, 218: 114982. Cited in this article [1]

[26]	Shi Y Q, Yang J L, Gao F, Zhang Q C. ACS Nano, 2023, 17(3): 1879. Cited in this article [1]

[27]	Corbett P T, Leclaire J, Vial L, West K R, Wietor J L, Sanders J K M, Otto S. Chem. Rev., 2006, 106(9): 3652. Cited in this article [1]

[28]	Jiang S Y, Gan S X, Zhang X, Li H, Qi Q Y, Cui F Z, Lu J, Zhao X. J. Am. Chem. Soc., 2019, 141(38): 14981. Cited in this article [1]

[29]	Jin E Q, Geng K Y, Lee K H, Jiang W M, Li J, Jiang Q H, Irle S, Jiang D L. Angew. Chem., 2020, 132(29): 12260. Cited in this article [1]

[30]	Chen Z A, Wang K, Tang Y M, Li L, Hu X N, Han M X, Guo Z Y, Zhan H B, Chen B L. Angewandte Chemie Int. Ed., 2023, 62(1): e202213268. Cited in this article [1]

[31]	Nguyen H L, Hanikel N, Lyle S J, Zhu C H, Proserpio D M, Yaghi O M. J. Am. Chem. Soc., 2020, 142(5): 2218. Cited in this article [1]

[32]	Xiong Y F, Liao Q B, Huang Z P, Huang X, Ke C, Zhu H T, Dong C Y, Wang H S, Xi K, Zhan P, Xu F, Lu Y Q. Adv. Mater., 2020, 32(9): 1907242. Cited in this article [2]

[33]	Lan Y S, Han X H, Tong M M, Huang H L, Yang Q Y, Liu D H, Zhao X, Zhong C L. Nat. Commun., 2018, 9: 5274. Cited in this article [1]

[34]	Kang X, Wu X W, Han X, Yuan C, Liu Y, Cui Y. Chem. Sci., 2020, 11(6): 1494. Cited in this article [2]

[35]	Nguyen H L, Gropp C, Ma Y H, Zhu C H, Yaghi O M. J. Am. Chem. Soc., 2020, 142(48): 20335. Cited in this article [1]

[36]	EL-Mahdy A F M, Mohamed M G, Mansoure T H, Yu H H, Chen T, Kuo S W. Chem. Commun., 2019, 55(99): 14890. Cited in this article [2]

[37]	Gong L, Gao Y, Wang Y H, Chen B T, Yu B Q, Liu W B, Han B, Lin C X, Bian Y Z, Qi D D, Jiang J Z. Catal. Sci. Technol., 2022, 12(21): 6566. Cited in this article [3]

[38]	Xing X L, Liao Q B, Ahmed S A, Wang D N, Ren S B, Qin X, Ding X L, Xi K, Ji L N, Wang K, Xia X H. Nano Lett., 2022, 22(3): 1358. Cited in this article [2]

[39]	Mohamed M G, Lee C C, EL-Mahdy A F M, Lüder J, Yu M H, Li Z, Zhu Z L, Chueh C C, Kuo S W. J. Mater. Chem. A, 2020, 8(22): 11448. Cited in this article [5]

[40]	Patra B C, Bhattacharya S. Chem. Mater., 2021, 33(21): 8512. Cited in this article [4]

[41]	Dalapati S, Jin E Q, Addicoat M, Heine T, Jiang D L. J. Am. Chem. Soc., 2016, 138(18): 5797. Cited in this article [2]

[42]	Liu Y Z, Diercks C S, Ma Y H, Lyu H, Zhu C H, Alshmimri S A, Alshihri S, Yaghi O M. J. Am. Chem. Soc., 2019, 141(1): 677. Cited in this article [1]

[43]	Peng L, Sun J, Huang J, Song C Y, Wang Q K, Wang L Q, Yan H G, Ji M B, Wei D P, Liu Y Q, Wei D C. Chem. Mater., 2022, 34(7): 2886. Cited in this article [3]

[44]	Chen X, Addicoat M, Jin E Q, Xu H, Hayashi T, Xu F, Huang N, Irle S, Jiang D L. Sci. Rep., 2015, 5: 14650. Cited in this article [1]

[45]	Pang Z F, Xu S Q, Zhou T Y, Liang R R, Zhan T G, Zhao X. J. Am. Chem. Soc., 2016, 138(14): 4710. Cited in this article [1]

[46]	Dong J Q, Li X, Peh S B, Yuan Y D, Wang Y X, Ji D X, Peng S J, Liu G L, Ying S M, Yuan D Q, Jiang J W, Ramakrishna S, Zhao D. Chem. Mater., 2019, 31(1): 146. Cited in this article [1]

[47]	Zhang B, Mao H Y, Matheu R, Reimer J A, Alshmimri S A, Alshihri S, Yaghi O M. J. Am. Chem. Soc., 2019, 141(29): 11420. Cited in this article [1]

[48]	Han X H, Chu J Q, Wang W Z, Qi Q Y, Zhao X. Chin. Chemical Lett., 2022, 33(5): 2464. Cited in this article [1]

[49]	Maschita J, Banerjee T, Lotsch B V. Chem. Mater., 2022, 34(5): 2249. Cited in this article [1]

[50]	Li W, Wang R, Jiang H X, Chen Y, Tang A N, Kong D M. Talanta, 2022, 236: 122829. Cited in this article [2]

[51]	Li X H, Tang H J, Gao L, Chen Z Y, Li H J, Wang Y H, Yang K X, Lu S Y, Wang K M, Zhou Q, Wang Z L. Polymer, 2022, 241: 124474. Cited in this article [2]

[52]	Rogge S M J, Bavykina A, Hajek J, Garcia H, Olivos-Suarez A I, Sepúlveda-Escribano A, Vimont A, Clet G, Bazin P, Kapteijn F, Daturi M, Ramos-Fernandez E V, Llabrés i Xamena F X, Van Speybroeck V, Gascon J. Chem. Soc. Rev., 2017, 46(11): 3134. Cited in this article [1]

[53]	Banerjee T, Gottschling K, Savasci G, Ochsenfeld C, Lotsch B V. ACS Energy Lett., 2018, 3(2): 400. Cited in this article [1]

[54]	Yan Y, He T, Zhao B, Qi K, Liu H F, Xia B Y. J. Mater. Chem. A, 2018, 6(33): 15905. Cited in this article [1]

[55]	Xu Z L, Cui X, Li Y H, Li Y W, Si Z J, Duan Q. Appl. Surf. Sci., 2023, 613: 155966. Cited in this article [3]

[56]	Sick T, Hufnagel A G, Kampmann J, Kondofersky I, Calik M, Rotter J M, Evans A, Döblinger M, Herbert S, Peters K, Böhm D, Knochel P, Medina D D, Fattakhova-Rohlfing D, Bein T. J. Am. Chem. Soc., 2018, 140(6): 2085. Cited in this article [1]

[57]	Rotter J M, Weinberger S, Kampmann J, Sick T, Shalom M, Bein T, Medina D D. Chem. Mater., 2019, 31(24): 10008. Cited in this article [1]

[58]	Yu H P, Zhang J Z, Yan X R, Wu C G, Zhu X R, Li B W, Li T F, Guo Q Q, Gao J F, Hu M J, Yang J. J. Mater. Chem. A, 2022, 10(20): 11010. Cited in this article [1]

[59]	Lv H W, Sa R J, Li P Y, Yuan D Q, Wang X C, Wang R H. Sci. China Chem., 2020, 63(9): 1289. Cited in this article [1]

[60]	He C, Si D H, Huang Y B, Cao R. Angewandte Chemie Int. Ed., 2022, 61(40): e202207478. Cited in this article [1]

[61]	Liu N, Shi L F, Han X H, Qi Q Y, Wu Z Q, Zhao X. Chin. Chemical Lett., 2020, 31(2): 386. Cited in this article [1]

[62]	Gao Q, Li X, Ning G H, Xu H S, Liu C B, Tian B B, Tang W, Loh K P. Chem. Mater., 2018, 30: 1762. Cited in this article [1]

[63]	Tian Y, Xu S Q, Qian C, Pang Z F, Jiang G F, Zhao X. Chem. Commun., 2016, 52(78): 11704. Cited in this article [1]

[64]	Zhang Q. Masteral Dissertation of Nanjing University, 2019. (张奇. 南京大学硕士论文, 2019.) Cited in this article [1]

[65]	Li J Y, He Y, Zou Y C, Yan Y, Song Z G, Shi X D. Chin. Chem. Lett., 2022, 33: 3017. Cited in this article [3]

[66]	Chen L J, Gong C T, Wang X K, Dai F N, Huang M C, Wu X W, Lu C Z, Peng Y W. J. Am. Chem. Soc., 2021, 143(27): 10243. Cited in this article [1]

[67]	Cui D, Ding X S, Xie W, Xu G J, Su Z M, Xu Y H, Xie Y Z. CrystEngComm, 2021, 23(33): 5569. Cited in this article [4]

[68]	Wang P, Xu Q, Li Z P, Jiang W M, Jiang Q H, Jiang D L. Adv. Mater., 2018, 30(29): 1801991. Cited in this article [1]

[69]	He L W, Chen L, Dong X L, Zhang S T, Zhang M X, Dai X, Liu X J, Lin P, Li K F, Chen C L, Pan T T, Ma F Y, Chen J C, Yuan M J, Zhang Y G, Chen L, Zhou R H, Han Y, Chai Z F, Wang S A. Chem, 2021, 7(3): 699. Cited in this article [3]

[70]	Lu Z X, Liu Y X, Liu X L, Lu S H, Li Y, Yang S X, Qin Y, Zheng L Y, Zhang H B. J. Mater. Chem. B, 2019, 7(9): 1469. Cited in this article [1]

[71]	Zhang W, Qiu L G, Yuan Y P, Xie A J, Shen Y H, Zhu J F. J. Hazard. Mater., 2012, 221/222: 147. Cited in this article [1]

[72]	Gao Q, Li X, Ning G H, Leng K, Tian B B, Liu C B, Tang W, Xu H S, Loh K P. Chem. Commun., 2018, 54(19): 2349. Cited in this article [3]

[73]	Faheem M, Aziz S, Jing X F, Ma T T, Du J Y, Sun F X, Tian Y Y, Zhu G S. J. Mater. Chem. A, 2019, 7(47): 27148. Cited in this article [1]

[74]	Ding H M. Doctoral Dissertation of Wuhan University, 2018. (丁慧敏. 武汉大学博士论文, 2018.). Cited in this article [1]

[75]	Xiu J, Zhang N, Li C, Salah A, Wang G. Microporous Mesoporous Mater., 2021, 316: 110979. Cited in this article [3]

[76]	Zheng M X, Yao C, Xie W, Xu Y H, Hu H. Bull. Chem. Soc. Jpn., 2021, 94(8): 2133. Cited in this article [1]

[77]	Cui F Z, Xie J J, Jiang S Y, Gan S X, Ma D L, Liang R R, Jiang G F, Zhao X. Chem. Commun., 2019, 55(31): 4550. Cited in this article [1]

[78]	Gong W, Dong Y J, Liu C Y, Shi H L, Yin M X, Li W J, Song Q B, Zhang C. Dyes Pigments, 2022, 204: 110464. Cited in this article [3]

[79]	Wu X C, Zhang X D, Li Y J, Wang B W, Li Y, Chen L G. J. Mater. Sci., 2021, 56(3): 2717. Cited in this article [1]

[80]	Wu X W, Han X, Xu Q S, Liu Y H, Yuan C, Yang S, Liu Y, Jiang J W, Cui Y. J. Am. Chem. Soc., 2019, 141(17): 7081. Cited in this article [3]

[81]	Song L L, Gao W Q, Wang S W, Bi H Q, Deng S Y, Cui L, Zhang C Y. Sens. Actuat. B Chem., 2022, 373: 132751. Cited in this article [1]

[82]	Dong J Q, Li X, Peh S B, Yuan Y D, Wang Y X, Ji D X, Peng S J, Liu G L, Ying S M, Yuan D Q, Jiang J W, Ramakrishna S, Zhao D. Chem. Mater., 2019, 31(1): 146. Cited in this article [3]

[83]	Li G R, Tian W C, Zhong C, Yang Y X, Lin Z A. ACS Appl. Mater. Interfaces, 2022, 14(18): 21750. Cited in this article [1]

[84]	Ding H M, Li J, Xie G H, Lin G Q, Chen R F, Peng Z K, Yang C L, Wang B S, Sun J L, Wang C. Nat. Commun., 2018, 9: 5234. Cited in this article [1]

[85]	Sun Q, Aguila B, Lan P C, Ma S Q. Adv. Mater., 2019, 31(19): 1900008. Cited in this article [1]

[86]	You J, Yuan F, Cheng S S, Kong Q Q, Jiang Y L, Luo X Z, Xian Y Z, Zhang C L. Chem. Mater., 2022, 34(15): 7078. Cited in this article [3]

[87]	Guo L, Jia S, Diercks C S, Yang X J, Alshmimri S A, Yaghi O M. Angew. Chem. Int. Ed., 2020, 59(5): 2023. Cited in this article [1]

[88]	Pang Z F, Zhou T Y, Liang R R, Qi Q Y, Zhao X. Chem. Sci., 2017, 8(5): 3866. Cited in this article [1]

[89]	Peng Y W, Li L X, Zhu C Z, Chen B, Zhao M T, Zhang Z C, Lai Z C, Zhang X, Tan C L, Han Y, Zhu Y H, Zhang H. J. Am. Chem. Soc., 2020, 142(30): 13162. Cited in this article [1]