Cooperative Supramolecular Polymerization of Propeller-Shaped Triphenylamine Cyanostilbenes for Explosive Detection

Long-Yu Guang; Zhi-Feng Zhou; Yi-Fei Zhang; Lai-Wei Gao; Feng Wang; Rui Liao

doi:10.1007/s10118-023-2917-3

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Cooperative Supramolecular Polymerization of Propeller-Shaped Triphenylamine Cyanostilbenes for Explosive Detection

RESEARCH ARTICLE | Updated：2023-03-07

- Cooperative Supramolecular Polymerization of Propeller-Shaped Triphenylamine Cyanostilbenes for Explosive Detection
- Cooperative Supramolecular Polymerization of Propeller-Shaped Triphenylamine Cyanostilbenes for Explosive Detection
- 高分子科学（英文版） 2023年41卷第4期页码：585-592
- Affiliations：
  
  a.CAS Key Laboratory of Soft Matter Chemistry, Department of Polymer Science and Engineering, University of Science and Technology of China, Hefei 230026, China
  b.Clinical Laboratory, The Second People’s Hospital of Hefei, Hefei 230011, China
- Author bio：
  
  drfwang@ustc.edu.cn (F.W.)
  rliao@ustc.edu.cn (R.L.)
- Funds：
  
  This work was financially supported by the National Natural Science Foundation of China (Nos. 21922110 and 21871245), the Collaborative Innovation Program of Hefei Science Center, CAS (No. 2022HSC-CIP014), and the Fundamental Research Funds for the Central Universities (No. WK3450000005). We are grateful for the technical support from the High Performance Computing Center of University of Science and Technology of China for DFT and TD-DFT computations.;Electronic supplementary information (ESI) is available free of charge in the online version of this article at http://doi.org/10.1007/s10118-023-2917-3.
- DOI：10.1007/s10118-023-2917-3
  中图分类号：
- 收稿：2022-10-21，
  
  修回：2022-11-22，
  
  录用：2022-12-1，
  
  网络首发：2023-01-16，
  
  纸质出版：2023-04-01
- Accepted：
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Guang, L. Y.; Zhou, Z. F.; Zhang, Y. F.; Gao, L. W.; Wang, F.; Liao, R. Cooperative supramolecular polymerization of propeller-shaped triphenylamine cyanostilbenes for explosive detection. Chinese J. Polym. Sci. 2023, 41, 585–592

Long-Yu Guang, Zhi-Feng Zhou, Yi-Fei Zhang, et al. Cooperative Supramolecular Polymerization of Propeller-Shaped Triphenylamine Cyanostilbenes for Explosive Detection[J]. Chinese Journal of Polymer Science, 2023, 41(4): 585-592.
Guang, L. Y.; Zhou, Z. F.; Zhang, Y. F.; Gao, L. W.; Wang, F.; Liao, R. Cooperative supramolecular polymerization of propeller-shaped triphenylamine cyanostilbenes for explosive detection. Chinese J. Polym. Sci. 2023, 41, 585–592 DOI： 10.1007/s10118-023-2917-3.

Long-Yu Guang, Zhi-Feng Zhou, Yi-Fei Zhang, et al. Cooperative Supramolecular Polymerization of Propeller-Shaped Triphenylamine Cyanostilbenes for Explosive Detection[J]. Chinese Journal of Polymer Science, 2023, 41(4): 585-592. DOI： 10.1007/s10118-023-2917-3.

摘要

A novel type of supramolecular polymers has been constructed on the basis of propeller-shaped triphenylamine cyanostilbenes. The resulting supramolecular polymers exhibit severe emission quenching upon addition of 2

6-dinitrotoluene

ascribed to photoinduced electron transfer from the triphenylamine cyanostilbenes to the explosive analyte.

Abstract

Self-assembly of

-conjugated compounds into supramolecular polymers has received considerable attention because of their intrinsic scientific interests and technological applications. As compared to

-conjugated rods

discotics

and macrocycles

propeller-shaped

-conjugated molecules have been less exploited to form long-range-ordered supramolecular polymers. Herein a novel type of supramolecular polymers has been constructed on the basis of propeller-shaped triphenylamine cyanostilbenes. The designed compound adopts nucleation−elongation cooperative mechanism for the supramolecular polymerization process

because of the participation of three-fold hydrogen bonds between the neighbouring monomers. The supramolecular polymeric state displays amplified chirality and enhanced emission than those in the monomeric state. The resulting supramolecular polymers exhibit severe emission quenching upon addition of 2

6-dinitrotoluene

ascribed to photoinduced electron transfer from the triphenylamine cyanostilbenes to the explosive analyte. The current study proves the feasibility to supramolecular polymerize propeller-like

-conjugated molecules

serving as a promising type of explosive sensor owing to their guest encapsulation and signal amplification capabilities.

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Keywords

references

Mako, T. L.; Racicot, J. M.; Levine, M . Supramolecular luminescent sensors . Chem. Rev. , 2019 . 119 322 - 477 . DOI: 10.1021/acs.chemrev.8b00260 http://doi.org/10.1021/acs.chemrev.8b00260 .

Xu D. A.; Zhou, Q. Y.; Dai, X.; Ma, X. K.; Zhang, Y. M.; Xu, X.; Liu, Y . Cucurbit[8]uril-mediated phosphorescent supramolecular foldamer for antibiotics sensing in water and cells . Chin. Chem. Lett. , 2022 . 33 851 - 854 . DOI: 10.1016/j.cclet.2021.08.001 http://doi.org/10.1016/j.cclet.2021.08.001 .

Yin, Z. H.; Yang, Y. C.; Yang, J. P.; Song, G. B.; Hu, H.; Zheng, P.; Xu, J. F . Supramolecular polymerization powered by escherichia coli : fabricating a near-infrared photothermal antibacterial agent in situ . CCS Chem. , 2022 . 4 3285 - 3295 . DOI: 10.31635/ccschem.021.202101490 http://doi.org/10.31635/ccschem.021.202101490 .

Yin, Z. H.; Song, G. B.; Jiao, Y.; Zheng, P.; Xu, J. F.; Zhang, X . Dissipative supramolecular polymerization powered by light . CCS Chem. , 2019 . 1 335 - 342 . DOI: 10.31635/ccschem.019.20190013 http://doi.org/10.31635/ccschem.019.20190013 .

Liu, K.; Jiang, Y. W.; Bao, Z.; Yan, X . Skin-inspired electronics enabled by supramolecular polymeric materials . CCS Chem. , 2019 . 1 431 - 447 . DOI: 10.31635/ccschem.019.20190048 http://doi.org/10.31635/ccschem.019.20190048 .

Wu, G. L.; Li, F.; Tang, B. H.; Zhang, X . Molecular engineering of noncovalent dimerization . J. Am. Chem. Soc., , 2022 . 144 14962 - 14975 . DOI: 10.1021/jacs.2c02434 http://doi.org/10.1021/jacs.2c02434 .

Jia, D.; Zhong, H.; Jiang, S.; Yao, R.; Wang, F . Simultaneous enhancement of phosphorescence and chirality by host-guest recognition of molecular tweezers . Chin. Chem. Lett. , 2022 . 33 4900 - 4903 . DOI: 10.1016/j.cclet.2022.02.081 http://doi.org/10.1016/j.cclet.2022.02.081 .

Yuan, W.; Cheng, J. J.; Li, X. P.; Wu, M. J.; Han, Y.; Yan, C. M.; Zou, G.; Müllen, K.; Chen, Y. L. . 5,6,12,13-Tetraazaperopyrenes as unique photonic and mechanochromic fluorophores . Angew. Chem. Int. Ed. , 2020 . 59 9940 - 9945 . DOI: 10.1002/anie.201914900 http://doi.org/10.1002/anie.201914900 .

Dumele, O.; Chen, J. H.; Passarelli, J. V.; Stupp, S. I . Supramolecular energy materials . Adv. Mater. , 2020 . 32 1907247 DOI: 10.1002/adma.201907247 http://doi.org/10.1002/adma.201907247 .

Han, Y.; Zhang, X.; Ge, Z.; Gao, Z.; Liao, R.; Wang, F . A bioinspired sequential energy transfer system constructed via supramolecular copolymerization . Nat. Commun. , 2022 . 13 3546 DOI: 10.1038/s41467-022-31094-w http://doi.org/10.1038/s41467-022-31094-w .

Zhang, X . Supramolecular polymer chemistry: past, present, and future . Chinese J. Polym. Sci. , 2022 . 40 541 - 542 . DOI: 10.1007/s10118-022-2748-7 http://doi.org/10.1007/s10118-022-2748-7 .

Li, Z.; Han, Y.; Nie, F.; Liu, M.; Zhong, H.; Wang, F . Bright and robust phosphorescence achieved by non-covalent clipping . Angew. Chem. Int. Ed. , 2021 . 60 8212 - 8219 . DOI: 10.1002/anie.202015846 http://doi.org/10.1002/anie.202015846 .

Qian, W. R.; Zuo, M. Z.; Niu, P. B.; Hu, X. Y.; Wang, L. Y . The construction of aggregation-induced charge transfer emission systems in aqueous solution directed by supramolecular strategy . Chin. Chem. Lett. , 2022 . 33 1975 - 1978 . DOI: 10.1016/j.cclet.2021.09.070 http://doi.org/10.1016/j.cclet.2021.09.070 .

Gao, Z.; Tian, Y.; Hsu, H.; Han, Y.; Chan, T.; Wang, F . Additive-controlled kinetic trapping of quadruple platinum(II) stacks with emergent photothermal behaviors . CCS Chem. , 2021 . 3 105 - 115 . DOI: 10.31635/ccschem.021.202000511 http://doi.org/10.31635/ccschem.021.202000511 .

Korlepara, D. B.; Henderson, W. R.; Castellano, R. K.; Balasubramanian, S . Differentiating the mechanism of self-assembly in supramolecular polymers through computation . Chem. Commun. , 2019 . 55 3773 DOI: 10.1039/C9CC01058K http://doi.org/10.1039/C9CC01058K .

Liao, R.; Wang, F.; Guo, Y.; Han, Y.; Wang, F . Chirality-controlled supramolecular donor-acceptor copolymerization with distinct energy transfer efficiency . J. Am. Chem. Soc. , 2022 . 144 9775 - 9784 . DOI: 10.1021/jacs.2c02270 http://doi.org/10.1021/jacs.2c02270 .

Xue, Y.; Jiang, S.; Zhong, H.; Chen, Z.; Wang, F . Photo-induced polymer cyclization via supramolecular confinement of cyanostilbenes . Angew. Chem. Int. Ed. , 2022 . 61 e202110766 DOI: 10.1002/ange.202110766 http://doi.org/10.1002/ange.202110766 .

de Greef, T. F. A.; Smulders, M. M. J.; Wolffs, M.; Schenning, A.; Sijbesma, R. P.; Meijer, E. W . Supramolecular polymerization . Chem. Rev. , 2009 . 109 5687 - 5754 . DOI: 10.1021/cr900181u http://doi.org/10.1021/cr900181u .

Han, Y.; Yin, Y.; Wang, F.; Wang, F . Single-photon near infrared responsiveness from molecular to supramolecular levels via platination of pentacenes . Angew. Chem. Int. Ed. , 2021 . 60 14076 DOI: 10.1002/anie.202103125 http://doi.org/10.1002/anie.202103125 .

Gao, Z.; Han, Y.; Wang, F . Cooperative supramolecular polymers with anthracene‒endoperoxide photo-switching for fluorescent anti-counterfeiting . Nat. Commun. , 2018 . 9 3977 DOI: 10.1038/s41467-018-06392-x http://doi.org/10.1038/s41467-018-06392-x .

Casellas, N. M.; Pujals, S.; Bochicchio, D.; Pavan, G. M.; Torres, T.; Albertazzi, L.; García-Iglesias, M . From isodesmic to highly cooperative: reverting the supramolecular polymerization mechanism in water by fine monomer design . Chem. Commun. , 2018 . 54 4112 - 4115 . DOI: 10.1039/C8CC01259H http://doi.org/10.1039/C8CC01259H .

Ślęczkowski, M. L.; Mabesoone, M. F. J.; Ślęczkowski, P.; Palmans, A. R. A.; Meijer, E. W . Competition between chiral solvents and chiral monomers in the helical bias of supramolecular polymers . Nat. Chem. , 2020 . 13 200 - 207 . DOI: 10.1038/s41557-020-00583-0 http://doi.org/10.1038/s41557-020-00583-0 .

Picini, F.; Schneider, S.; Gavat, O.; Vargas Jentzsch, A.; Ta, J. J.; Maaloum, M.; Strub, J. M.; Tokunaga, S.; Lehn, J. M.; Moulin, E.; Giuseppone, N . Supramolecular polymerization of triarylamine based macrocycles into electroactive nanotubes . J. Am. Chem. Soc. , 2021 . 143 6498 DOI: 10.1021/jacs.1c00623 http://doi.org/10.1021/jacs.1c00623 .

Wang, Q. H.; Zhong, Y. L.; Mille, D. P.; Lu, X. X.; Tang, Q.; Lu, Z. L.; Zurek E.; Liu R.; Gong, B . Self-assembly and molecular recognition in water: tubular stacking and guest-templated discrete assembly of water-soluble, shape-persistent macrocycles . J. Am. Chem. Soc. , 2020 . 142 2915 - 2924 . DOI: 10.1021/jacs.9b11536 http://doi.org/10.1021/jacs.9b11536 .

Kim, T.; Mori, T.; Aida, T.; Miyajima, D . Dynamic propeller conformation for the unprecedentedly high degree of chiral amplification of supramolecular helices . Chem. Sci. , 2016 . 7 6689 - 6694 . DOI: 10.1039/C6SC02814D http://doi.org/10.1039/C6SC02814D .

Stewart, J. J. P . Optimization of parameters for semiempirical methods VI: more modifications to the NDDO approximations and reoptimization of parameters . J. Mol. Model. , 2013 . 19 1 - 32 . DOI: 10.1007/s00894-012-1667-x http://doi.org/10.1007/s00894-012-1667-x .

James, J. P. Stewart. MOPAC2016; Stewart Computational Chemistry. http://openmopac.net/.

Huang, H.; Chen, Z. H.; Ortiz, R. P.; Newman, C.; Usta, H.; Lou, S.; Youn, J.; Noh, Y. Y.; Baeg, K. J.; Chen, L. X.; Facchett, A.; Marks, T. J . Combining electron-neutral building blocks with intramolecular “conformational locks” affords stable, high-mobility pand N-channel polymer semiconductors . J. Am. Chem. Soc. , 2012 . 134 10966 - 10973 . DOI: 10.1021/ja303401s http://doi.org/10.1021/ja303401s .

Rowland, R. S.; Taylor, R. J . Intermolecular nonbonded contact distances in organic crystal structures: comparison with distances expected from van der Waals radii . Phys. Chem. , 1996 . 100 7384 DOI: 10.1021/jp953141+ http://doi.org/10.1021/jp953141+ .

Sun, Z. B.; Li, S. Y.; Liu, Z. Q.; Zhao, C. H . Triarylborane π -electron systems with intramolecular charge-transfer transitions . Chin. Chem. Lett. , 2016 . 27 1131 - 1138 . DOI: 10.1016/j.cclet.2016.06.007 http://doi.org/10.1016/j.cclet.2016.06.007 .

Zhao, D. H.; Moore, J. S . Nucleation-elongation: a mechanism for cooperative supramolecular polymerization . Org. Biomol. Chem. , 2003 . 1 3471 - 3491 . DOI: 10.1039/B308788C http://doi.org/10.1039/B308788C .

Wagner, W.; Wehner, M.; Stepanenko, V.; Würthner, F . Impact of molecular shape on supramolecular copolymer synthesis in seeded living polymerization of perylene bisimides . CCS Chem. , 2019 . 2 598 - 613 . DOI: 10.31635/ccschem.019.20190061 http://doi.org/10.31635/ccschem.019.20190061 .

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