Abstract
Charged metal-organic cages generally produce aggregates with various morphologies and different properties through the multiple supramolecular interactions in solution. Herein, a luminescent hexahedral metal-organic cage containing pyrene chromophores is successfully constructed through coordination-driven subcomponent self-assembly. The cage exhibits novel spontaneous aggregation in a dilute solution and time-dependent luminescence enhancement behavior during the subsequent incubation process. Dynamic light scatter (DLS) and transmission electron microscopy (TEM) results prove that the metal-organic cages can form blackberry-like aggregates in methanol dilute solution. Unexpectedly, the luminescent intensity of this system shows a linear increase with the extension of the incubation time in methanol, and this process is also reflected in the change in the quantum yield of the system (2% to over 80% after 5 days incubation time). Ultraviolet-visible (UV-vis), 1H nuclear magnetic resonance (1H NMR) and mass spectra show that metal-organic cages can stably exist in dilute solution. Time-depended DLS and TEM data reveal that the aggregates of metal-organic cages are gradually changed from the dense state to the loose one, which may involve the transition of the system from an energy unstable state to a stable one, probably leading to the unusual time-dependent luminescent property. This unique time-dependent luminescent cage aggregate can be potentially applied as a “supramolecular time meter”.
Similar content being viewed by others
Change history
12 December 2022
An Erratum to this paper has been published: https://doi.org/10.1007/s11426-022-1482-y
References
Furukawa H, Cordova KE, O’Keeffe M, Yaghi OM. Science, 2013, 341: 1230444
Cook TR, Stang PJ. Chem Rev, 2015, 115: 7001–7045
Rizzuto FJ, von Krbek LKS, Nitschke JR. Nat Rev Chem, 2019, 3: 204–222
Howlader P, Zangrando E, Mukherjee PS. J Am Chem Soc, 2020, 142: 9070–9078
Niki K, Tsutsui T, Yamashina M, Akita M, Yoshizawa M. Angew Chem Int Ed, 2020, 59: 10489–10492
Brown CJ, Toste FD, Bergman RG, Raymond KN. Chem Rev, 2015, 115: 3012–3035
Jin Y, Zhang Q, Zhang Y, Duan C. Chem Soc Rev, 2020, 49: 5561–5600
Jiao J, Li Z, Qiao Z, Li X, Liu Y, Dong J, Jiang J, Cui Y. Nat Commun, 2018, 9: 4423
Therrien B, Süss-Fink G, Govindaswamy P, Renfrew AK, Dyson PJ. Angew Chem Int Ed, 2008, 47: 3773–3776
Yu G, Cook TR, Li Y, Yan X, Wu D, Shao L, Shen J, Tang G, Huang F, Chen X, Stang PJ. Proc Natl Acad Sci USA, 2016, 113: 13720–13725
Fang Y, Lian X, Huang Y, Fu G, Xiao Z, Wang Q, Nan B, Pellois JP, Zhou HC. Small, 2018, 14: 1802709
Wang Z, He L, Liu B, Zhou LP, Cai LX, Hu SJ, Li XZ, Li Z, Chen T, Li X, Sun QF. J Am Chem Soc, 2020, 142: 16409–16419
Neelakandan PP, Jiménez A, Nitschke JR. Chem Sci, 2014, 5: 908–915
Yamashina M, Tsutsui T, Sei Y, Akita M, Yoshizawa M. Sci Adv, 2019, 5: eaav3179
Caulder DL, Raymond KN. Acc Chem Res, 1999, 32: 975–982
Percástegui EG, Ronson TK, Nitschke JR. Chem Rev, 2020, 120: 13480–13544
Yamashina M, Tanaka Y, Lavendomme R, Ronson TK, Pittelkow M, Nitschke JR. Nature, 2019, 574: 511–515
Turega S, Cullen W, Whitehead M, Hunter CA, Ward MD. J Am Chem Soc, 2014, 136: 8475–8483
Mosquera J, Szyszko B, Ho SKY, Nitschke JR. Nat Commun, 2017, 8: 14882
Zhou XP, Wu Y, Li D. J Am Chem Soc, 2013, 135: 16062–16065
Luo D, Zhou XP, Li D. Angew Chem Int Ed, 2015, 54: 6190–6195
Fujita M, Tominaga M, Hori A, Therrien B. Acc Chem Res, 2005, 38: 369–378
Jansze SM, Severin K. Acc Chem Res, 2018, 51: 2139–2147
Tan C, Jiao J, Li Z, Liu Y, Han X, Cui Y. Angew Chem Int Ed, 2018, 57: 2085–2090
Olenyuk B, Levin MD, Whiteford JA, Shield JE, Stang PJ. J Am Chem Soc, 1999, 121: 10434–10435
Pasquale S, Sattin S, Escudero-Adán EC, Martínez-Belmonte M, de Mendoza J. Nat Commun, 2012, 3: 785
Bilbeisi RA, Ronson TK, Nitschke JR. Angew Chem Int Ed, 2013, 52: 9027–9030
Sun QF, Iwasa J, Ogawa D, Ishido Y, Sato S, Ozeki T, Sei Y, Yamaguchi K, Fujita M. Science, 2010, 328: 1144–1147
Fujita D, Ueda Y, Sato S, Yokoyama H, Mizuno N, Kumasaka T, Fujita M. Chem, 2016, 1: 91–101
Saha S, Regeni I, Clever GH. Coord Chem Rev, 2018, 374: 1–14
Zhou XP, Liu J, Zhan SZ, Yang JR, Li D, Ng KM, Sun RWY, Che CM. J Am Chem Soc, 2012, 134: 8042–8045
Luo D, Wang XZ, Yang C, Zhou XP, Li D. J Am Chem Soc, 2018, 140: 118–121
Shao L, Hu X, Sikligar K, Baker GA, Atwood JL. Acc Chem Res, 2021, 54: 3191–3203
Raee E, Yang Y, Liu T. Giant, 2021, 5: 100050
Fu J, Schlenoff JB. J Am Chem Soc, 2016, 138: 980–990
Li D, Zhang J, Landskron K, Liu T. J Am Chem Soc, 2008, 130: 4226–4227
Li D, Zhou W, Landskron K, Sato S, Kiely CJ, Fujita M, Liu T. Angew Chem Int Ed, 2011, 50: 5182–5187
Yang Y, Rehak P, Xie TZ, Feng Y, Sun X, Chen J, Li H, Král P, Liu T. ACS Appl Mater Interfaces, 2020, 12: 56310–56318
Sun Y, Yao Y, Wang H, Fu W, Chen C, Saha ML, Zhang M, Datta S, Zhou Z, Yu H, Li X, Stang PJ. J Am Chem Soc, 2018, 140: 12819–12828
Sun Y, Zhang F, Jiang S, Wang Z, Ni R, Wang H, Zhou W, Li X, Stang PJ. J Am Chem Soc, 2018, 140: 17297–17307
Chen M, Wang J, Liu D, Jiang Z, Liu Q, Wu T, Liu H, Yu W, Yan J, Wang P. J Am Chem Soc, 2018, 140: 2555–2561
Raee E, Li H, Sun X, Ustriyana P, Luo J, Chen J, Sahai N, Liu T. J Phys Chem B, 2020, 124: 9958–9966
Yoshizawa M, Catti L. Acc Chem Res, 2019, 52: 2392–2404
Jing X, He C, Zhao L, Duan C. Acc Chem Res, 2019, 52: 100–109
Musser AJ, P Neelakandan P, Richter JM, Mori H, Friend RH, Nitschke JR. J Am Chem Soc, 2017, 139: 12050–12059
Li XZ, Zhou LP, Yan LL, Yuan DQ, Lin CS, Sun QF. J Am Chem Soc, 2017, 139: 8237–8244
Luo D, Li M, Zhou XP, Li D. Chem Eur J, 2018, 24: 7108–7113
Guo XQ, Zhou LP, Cai LX, Sun QF. Chem Eur J, 2018, 24: 6936–6940
Zhang M, Saha ML, Wang M, Zhou Z, Song B, Lu C, Yan X, Li X, Huang F, Yin S, Stang PJ. J Am Chem Soc, 2017, 139: 5067–5074
Yamashina M, Sartin MM, Sei Y, Akita M, Takeuchi S, Tahara T, Yoshizawa M. J Am Chem Soc, 2015, 137: 9266–9269
Hou Y, Zhang Z, Lu S, Yuan J, Zhu Q, Chen WP, Ling S, Li X, Zheng YZ, Zhu K, Zhang M. J Am Chem Soc, 2020, 142: 18763–18768
Yang D, von Krbek LKS, Yu L, Ronson TK, Thoburn JD, Carpenter JP, Greenfield JL, Howe DJ, Wu B, Nitschke JR. Angew Chem Int Ed, 2021, 60: 4485–4490
Yamashina M, Akita M, Hasegawa T, Hayashi S, Yoshizawa M. Sci Adv, 2017, 3: e1701126
Lu C, Zhang M, Tang D, Yan X, Zhang ZY, Zhou Z, Song B, Wang H, Li X, Yin S, Sepehrpour H, Stang PJ. J Am Chem Soc, 2018, 140: 7674–7680
Chen LJ, Yang HB. Acc Chem Res, 2018, 51: 2699–2710
Dong J, Pan Y, Wang H, Yang K, Liu L, Qiao Z, Yuan YD, Peh SB, Zhang J, Shi L, Liang H, Han Y, Li X, Jiang J, Liu B, Zhao D. Angew Chem Int Ed, 2020, 59: 10151–10159
Zhao J, Zhou Z, Li G, Stang PJ, Yan X. Natl Sci Rev, 2021, 8: nwab045
Yan X, Cook TR, Wang P, Huang F, Stang PJ. Nat Chem, 2015, 7: 342–348
Kleywegt GJ, Jones TA. Acta Crystlogr D Biol Crystlogr, 1994, 50: 178–185
Takahashi O, Kohno Y, Nishio M. Chem Rev, 2010, 110: 6049–6076
Figueira-Duarte TM, Müllen K. Chem Rev, 2011, 111: 7260–7314
Islam MM, Hu Z, Wang Q, Redshaw C, Feng X. Mater Chem Front, 2019, 3: 762–781
Wang J, Dang Q, Gong Y, Liao Q, Song G, Li Q, Li Z. CCS Chem, 2021, 3: 274–286
Saha S, Holzapfel B, Chen YT, Terlinden K, Lill P, Gatsogiannis C, Rehage H, Clever GH. J Am Chem Soc, 2018, 140: 17384–17388
Li H, Xie TZ, Liang Z, Shen Y, Sun X, Yang Y, Liu T. J Phys Chem C, 2019, 123: 23280–23286
Claessens CG, Stoddart JF. J Phys Org Chem, 1997, 10: 254–272
Huang Z, Jiang T, Wang J, Ma X, Tian H. Angew Chem Int Ed, 2021, 60: 2855–2860
Zhang J, Liu Q, Wu W, Peng J, Zhang H, Song F, He B, Wang X, Sung HHY, Chen M, Li BS, Liu SH, Lam JWY, Tang BZ. ACS Nano, 2019, 13: 3618–3628
Nishino K, Yamamoto H, Ochi J, Tanaka K, Chujo Y. Chem Asian J, 2019, 14: 1577–1581
Fujiki M, Yoshida K, Suzuki N, Rahim NAA, Jalil JA. J Photochem Photobiol A-Chem, 2016, 331: 120–129
Fujiki M, Yoshimoto S. Mater Chem Front, 2017, 1: 1773–1785
Zhang C, Yin AX, Jiang R, Rong J, Dong L, Zhao T, Sun LD, Wang J, Chen X, Yan CH. ACS Nano, 2013, 7: 4561–4568
Acknowledgements
This work was supported by the Guangdong Major Project of Basic and Applied Research (2019B030302009), the National Natural Science Foundation of China (22171106, 21731002, 21975104, 21871172), the Guangzhou Science and Technology Program (202002030411), and Jinan University.
Author information
Authors and Affiliations
Corresponding author
Additional information
Conflict of interest
The authors declare no conflict of interest.
Supporting information
The supporting information is available online at http://chem.scichina.com and http://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_2022_1245_MOESM1_ESM.pdf
Self-assembly of a photoluminescent metal-organic cage and its spontaneous aggregation in dilute solutions enabling time-dependent emission enhancement
Rights and permissions
About this article
Cite this article
Luo, D., Wu, LX., Zhang, Y. et al. Self-assembly of a photoluminescent metal-organic cage and its spontaneous aggregation in dilute solutions enabling time-dependent emission enhancement. Sci. China Chem. 65, 1105–1111 (2022). https://doi.org/10.1007/s11426-022-1245-1
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11426-022-1245-1