Abstract
The development of preparation methods for XOFs, as a new class of organic frameworks, plays a crucial role in shaping their structures, functions, and potential applications. In this study, we presented the construction of chiral supramolecular 2D halogen-bonded organic frameworks (XOFs) through a post-synthetic modification strategy. A linear halogen-bonded organic polymer (XOP), XOP-DPBA, decorated with aldehyde groups, was initially prepared to validate the feasibility of post-synthetic modification for XOF construction and functionalization. XOP-DPBA exhibited excellent reactivity with amines, forming imine bonds. By utilizing this reactivity, a series of cross-linked 2D XOFs were efficiently prepared through post-synthetic modified cross-linking reactions. Furthermore, we successfully introduced chiral α/β-cyclodextrins (α/β-CD) into the XOF skeletons via host-guest interactions, resulting in the fabrication of chiral supramolecular 2D XOFs. These chiral XOFs displayed the induced circular dichroism (ICD) signals and assembled them into helical fibers. The post-synthetic modification strategy demonstrated its versatility and simplicity for the construction and functionalization of XOFs.
Similar content being viewed by others
References
Liu R, Tan KT, Gong Y, Chen Y, Li Z, Xie S, He T, Lu Z, Yang H, Jiang D. Chem Soc Rev, 2021, 50: 120–242
Qiu T, Gao S, Liang Z, Wang D, Tabassum H, Zhong R, Zou R. Angew Chem Int Ed, 2021, 60: 17314–17336
Freund R, Zaremba O, Arnauts G, Ameloot R, Skorupskii G, Dincă M, Bavykina A, Gascon J, Ejsmont A, Goscianska J, Kalmutzki M, Lächelt U, Ploetz E, Diercks CS, Wuttke S. Angew Chem Int Ed, 2021, 60: 23975–24001
Zhao X, Pachfule P, Thomas A. Chem Soc Rev, 2021, 50: 6871–6913
He Y, Xiang S, Chen B. J Am Chem Soc, 2011, 133: 14570–14573
Liu Y, Wang ZK, Liu CZ, Liu YY, Li Q, Wang H, Cui F, Zhang DW, Li ZT. ACS Appl Mater Interfaces, 2022, 14: 47397–47408
Gui B, Liu X, Cheng Y, Zhang Y, Chen P, He M, Sun J, Wang C. Angew Chem Int Ed, 2022, 61: e202113852
Kandambeth S, Dey K, Banerjee R. J Am Chem Soc, 2019, 141: 1807–1822
Liu Y, Ma Y, Yang J, Diercks CS, Tamura N, Jin F, Yaghi OM. J Am Chem Soc, 2018, 140: 16015–16019
Ding M, Flaig RW, Jiang HL, Yaghi OM. Chem Soc Rev, 2019, 48: 2783–2828
Rodenas T, Luz I, Prieto G, Seoane B, Miro H, Corma A, Kapteijn F, Llabrés i Xamena FX, Gascon J. Nat Mater, 2015, 14: 48–55
Han YF, Yuan YX, Wang HB. Molecules, 2017, 22: 266
Hisaki I, Xin C, Takahashi K, Nakamura T. Angew Chem Int Ed, 2019, 58: 11160–11170
Wang H, Li B, Wu H, Hu TL, Yao Z, Zhou W, Xiang S, Chen B. J Am Chem Soc, 2015, 137: 9963–9970
Liu B, Pan X, Nie D, Hu X, Liu E, Liu T. Adv Mater, 2020, 32: 2005912
Liu B, Pan X, Zhang D, Wang R, Chen J, Fang H, Liu T. Angew Chem Int Ed, 2021, 60: 25701–25707
Yin Q, Zhao P, Sa R, Chen G, Lü J, Liu T, Cao R. Angew Chem Int Ed, 2018, 57: 7691–7696
Li ZT, Yu SB, Liu Y, Tian J, Zhang DW. Acc Chem Res, 2022, 55: 2316–2325
Xu W, Chao J, Tang B, Li Z, Xu J, Zhang X. Chem Eur J, 2022, 28: e202202200
Yin ZJ, Jiang SY, Liu N, Qi QY, Wu ZQ, Zhan TG, Zhao X. CCS Chem, 2022, 4: 141–150
Han X, Xia Q, Huang J, Liu Y, Tan C, Cui Y. J Am Chem Soc, 2017, 139: 8693–8697
Ji J, Liu F, Yang W, Tan M, Luo W, Yin S. ChemCatChem, 2020, 12: 4331–4338
Si Y, Wang W, El-Sayed ESM, Yuan D. Sci China Chem, 2020, 63: 881–889
Wang Z, Zhu Q, Wang J, Jin F, Zhang P, Yan D, Cheng P, Chen Y, Zhang Z. Sci China Chem, 2022, 65: 2144–2162
Ye ZM, Zhang XF, Liu DX, Xu YT, Wang C, Zheng K, Zhou DD, He CT, Zhang JP. Sci China Chem, 2022, 65: 1552–1558
Keller N, Bein T. Chem Soc Rev, 2020, 50: 1813–1845
Liang C, Cheng L, Zhang S, Yang S, Liu W, Xie J, Li MD, Chai Z, Wang Y, Wang S. J Am Chem Soc, 2022, 144: 2189–2196
Bhunia S, Deo KA, Gaharwar AK. Adv Funct Mater, 2020, 30: 2002046
Sun Y, Zheng L, Yang Y, Qian X, Fu T, Li X, Yang Z, Yan H, Cui C, Tan W. Nano-Micro Lett, 2020, 12: 103
Lin F, Yu S, Liu Y, Liu C, Lu S, Cao J, Qi Q, Zhou W, Li X, Liu Y, Tian J, Li Z. Adv Mater, 2022, 34: 2200549
Gong G, Lv S, Han J, Xie F, Li Q, Xia N, Zeng W, Chen Y, Wang L, Wang J, Chen S. Angew Chem Int Ed, 2021, 60: 14831–14835
Gong G, Zhao J, Chen Y, Xie F, Lu F, Wang J, Wang L, Chen S. J Mater Chem A, 2022, 10: 10586–10592
Ke Z, Cheng Y, Yang S, Li F, Ding L. Int J Hydrogen Energy, 2017, 42: 11461–11468
Lustig WP, Mukherjee S, Rudd ND, Desai AV, Li J, Ghosh SK. Chem Soc Rev, 2017, 46: 3242–3285
Hao J, Xu X, Fei H, Li L, Yan B. Adv Mater, 2018, 30: 1705634
Kaur M, Kumar S, Yusuf M, Lee J, Brown RJC, Kim KH, Malik AK. Coord Chem Rev, 2021, 449: 214214
Segura JL, Royuela S, Mar Ramos M. Chem Soc Rev, 2019, 48: 3903–3945
Wu YP, Yang B, Tian J, Yu SB, Wang H, Zhang DW, Liu Y, Li ZT. Chem Commun, 2017, 53: 13367–13370
Liu C, Jiang Y, Nalaparaju A, Jiang J, Huang A. J Mater Chem A, 2019, 7: 24205–24210
Wang Z, Cohen SM. J Am Chem Soc, 2007, 129: 12368–12369
Yu B, Li L, Liu S, Wang H, Liu H, Lin C, Liu C, Wu H, Zhou W, Li X, Wang T, Chen B, Jiang J. Angew Chem Int Ed, 2021, 60: 8983–8989
Sun Q, Aguila B, Earl LD, Abney CW, Wojtas L, Thallapally PK, Ma S. Adv Mater, 2018, 30: 1705479
Kou WT, Yang CX, Yan XP. J Mater Chem A, 2018, 6: 17861–17866
Kodaka M. J Phys Chem, 1991, 95: 2110–2112
Shimizu H, Kaito A, Hatano M. Bull Chem Soc Jpn, 1979, 52: 2678–2684
Xia N, Han J, Xie F, Gong G, Wang L, Wang J, Chen S. ACS Appl Mater Interfaces, 2022, 14: 43621–43627
Naumkin AV, Kraut VA, Gaarenstroom SW, Powell CJ. NIST X-ray Photoelectron Spectroscopy Database. 2012
Zhang W, Zhou L, Shi J, Deng H. J Colloid Interface Sci, 2017, 496: 167–176
Chakrabarty R, Stang PJ. J Am Chem Soc, 2012, 134: 14738–14741
Gao S, Yang G, Zhang X, Lu Y, Chen Y, Wu X, Song C. ACS Omega, 2022, 7: 12747–12752
Hou J, Guo J, Yan T, Liu S, Zang M, Wang L, Xu J, Luo Q, Wang T, Liu J. Chem Sci, 2023, 14: 6039–6044
Wang W, He X, Wang X, Zhao T, Muraoka O, Tanabe G, Xie W, Zhou T, Xing L, Jin Q, Jiang H. Chin Chem Lett, 2023, 34: 108656
Hu L, Zhu X, Yang C, Liu M. Angew Chem Int Ed, 2022, 61: e202114759
Li Y, Liu M. J Colloid Interface Sci, 2007, 306: 386–390
Wang X, Li M, Song P, Lv X, Liu Z, Huang J, Yan Y. Chem Eur J, 2018, 24: 13734–13739
Liu Y, Ma Y, Yang J, Diercks CS, Tamura N, Jin F, Yaghi OM. J Am Chem Soc, 2018, 140: 16015–16019
Das G, Garai B, Prakasam T, Benyettou F, Varghese S, Sharma SK, Gándara F, Pasricha R, Baias M, Jagannathan R, Saleh N’, Elhabiri M, Olson MA, Trabolsi A. Nat Commun, 2022, 13: 3904
Liu Y, Ma Y, Zhao Y, Sun X, Gándara F, Furukawa H, Liu Z, Zhu H, Zhu C, Suenaga K, Oleynikov P, Alshammari AS, Zhang X, Terasaki O, Yaghi OM. Science, 2016, 351: 365–369
Acknowledgements This work was supported by the National Natural Science Foundation of China (22371218, 21702153, 21801194) and the Wuhan Science and Technology Bureau (whkxjsj009). We thank the support of the Core Facility of Wuhan University and the Large-scale Instrument and Equipment Sharing Foundation of Wuhan University. We thank Miss Dai from the Core Facility of Wuhan University for her assistance with SEM analysis.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
Conflict of interest The authors declare no conflict of interest.
Additional information
Supporting information The supporting information is available online at chem.scichina.com and link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.
Supporting Information
11426_2023_1829_MOESM1_ESM.docx
Chiral Supramolecular 2D Halogen-Bonded Organic Frame-works Constructed by Post-Synthetic Modified Cross-Linking Strategy
Rights and permissions
About this article
Cite this article
Xia, N., Zhao, J., Gong, G. et al. Chiral supramolecular 2D halogen-bonded organic frameworks constructed by post-synthetic modified cross-linking strategy. Sci. China Chem. 66, 3169–3177 (2023). https://doi.org/10.1007/s11426-023-1829-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-023-1829-8