CC BY-NC-ND 4.0 · Synlett 2022; 33(09): 875-878
DOI: 10.1055/s-0040-1720924
cluster
Mechanochemistry

Triazole-Extended Anthracenes as Optical Force Probes

Christoph Baumann 
a   DWI – Leibniz Institute for Interactive Materials, Forckenbeckstr. 50, 52056 Aachen, Germany
b   Institute of Technical and Macromolecular Chemistry, RWTH Aachen University, Worringerweg 1, 52074 Aachen, Germany
,
Robert Göstl  ∗
a   DWI – Leibniz Institute for Interactive Materials, Forckenbeckstr. 50, 52056 Aachen, Germany
› InstitutsangabenC.B. and R.G. are grateful for support by a Freigeist-Fellowship of the Volkswagen Foundation (92888). Parts of the analytical investigations were performed at the Center for Chemical Polymer Technology CPT, which was supported by the European Commission and the federal state of North Rhine-Westphalia (300088302). Financial support is acknowledged from the European Commission (EUSMI, 731019).
› Weitere Informationen
   Lizenzen und Reprints Alle Artikel dieser Rubrik


Abstract

Optical force probes (OFPs) are force-responsive molecules that report on mechanically induced transformations by the alteration of their optical properties. Yet, their modular design and incorporation into polymer architectures at desired positions is challenging. Here we report triazole-extended anthracene OFPs that combine two modular ‘click’ reactions in their synthesis potentially allowing their incorporation at desirable positions in complex polymer materials. Importantly, these retain the excellent optical properties of their parent 9-π-extended anthracene OFP counterparts.

Key words

mechanochemistry - fluorescence - polymers - cycloaddition - chromophores

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1720924.
  • Supporting Information

Primary Data

    Primary data for this article are available online at https://zenodo.org/record/5175871 and can be cited using the following DOI: 10.5281/zenodo.5175871.



Publikationsverlauf

Eingereicht: 11. August 2021

Angenommen nach Revision: 16. September 2021

Artikel online veröffentlicht:
14. Oktober 2021

© 2021. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution-NonDerivative-NonCommercial-License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by-nc-nd/4.0/)

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany

 

  • References and Notes

  • 1 O’Neill RT, Boulatov R. Nat. Rev. Chem. 2021; 5: 148
    CrossrefPubMed
  • 2 Chen Y, Mellot G, van Luijk D, Creton C, Sijbesma RP. Chem. Soc. Rev. 2021; 50: 4100
    CrossrefPubMed
  • 3 Yuan Y, Yuan W, Chen Y. Sci. China Mater. 2016; 59: 507
    Crossref
  • 4 Göstl, R.; Clough, J. M.; Sijbesma, R. P. In Mechanochemistry in Materials Craig S. L.; Royal Society of Chemistry, London, 2017; 53.
  • 5 Traeger H, Kiebala DJ, Weder C, Schrettl S. Macromol. Rapid Commun. 2021; 42: 2000573
    CrossrefPubMed
  • 6 Davis DA, Hamilton A, Yang J, Cremar LD, Van Gough D, Potisek SL, Ong MT, Braun PV, Martínez TJ, White SR, Moore JS, Sottos NR. Nature 2009; 459: 68
    CrossrefPubMed
  • 7 Li J, Nagamani C, Moore JS. Acc. Chem. Res. 2015; 48: 2181
    CrossrefPubMed
  • 8 Chen Y, Spiering AJ. H, Karthikeyan S, Peters GW. M, Meijer EW, Sijbesma RP. Nat. Chem. 2012; 4: 559
    CrossrefPubMed
  • 9 Ducrot E, Chen Y, Bulters M, Sijbesma RP, Creton C. Science 2014; 344: 186
    CrossrefPubMed
  • 10 Imato K, Irie A, Kosuge T, Ohishi T, Nishihara M, Takahara A, Otsuka H. Angew. Chem. Int. Ed. 2015; 54: 6168
    CrossrefPubMed
  • 11 Kosuge T, Zhu X, Lau VM, Aoki D, Martinez TJ, Moore JS, Otsuka H. J. Am. Chem. Soc. 2019; 141: 1898
    CrossrefPubMed
  • 12 Kato S, Furukawa S, Aoki D, Goseki R, Oikawa K, Tsuchiya K, Shimada N, Maruyama A, Numata K, Otsuka H. Nat. Commun. 2021; 12: 126
    CrossrefPubMed
  • 13 Löwe C, Weder C. Adv. Mater. 2002; 14: 1625
    Crossref
  • 14 Traeger H, Sagara Y, Kiebala DJ, Schrettl S, Weder C. Angew. Chem. Int. Ed. 2021; 60: 16191
    CrossrefPubMed
  • 15 Sagara Y, Traeger H, Li J, Okado Y, Schrettl S, Tamaoki N, Weder C. J. Am. Chem. Soc. 2021; 143: 5519
    CrossrefPubMed
  • 16 Konda SS. M, Brantley JN, Varghese BT, Wiggins KM, Bielawski CW, Makarov DE. J. Am. Chem. Soc. 2013; 135: 12722
    CrossrefPubMed
  • 17 Li J, Shiraki T, Hu B, Wright RA. E, Zhao B, Moore JS. J. Am. Chem. Soc. 2014; 136: 15925
    CrossrefPubMed
  • 18 Noh J, Peterson GI, Choi T.-L. Angew. Chem. Int. Ed. 2021; 60: 18651
    CrossrefPubMed
  • 19 Göstl R, Sijbesma RP. Chem. Sci. 2016; 7: 370
    CrossrefPubMed
  • 20 Yildiz D, Baumann C, Mikosch A, Kuehne AJ. C, Herrmann A, Göstl R. Angew. Chem. Int. Ed. 2019; 58: 12919
    CrossrefPubMed
  • 21 Baumann C, Stratigaki M, Centeno SP, Göstl R. Angew. Chem. Int. Ed. 2021; 60: 13287
    CrossrefPubMed
  • 22 Izak-Nau E, Demco DE, Braun S, Baumann C, Pich A, Göstl R. ACS Appl. Polym. Mater. 2020; 2: 1682
    Crossref
  • 23 Willis-Fox N, Rognin E, Baumann C, Aljohani TA, Göstl R, Daly R. Adv. Funct. Mater. 2020; 30: 2002372
    Crossref
  • 24 Stratigaki M, Baumann C, van Breemen LC. A, Heuts JP. A, Sijbesma RP, Göstl R. Polym. Chem. 2020; 11: 358
    Crossref
  • 25 Slootman J, Waltz V, Yeh CJ, Baumann C, Göstl R, Comtet J, Creton C. Phys. Rev. X 2020; 10: 041045
  • 26 Morelle XP, Sanoja GE, Castagnet S, Creton C. Soft Matter 2021; 17: 4266
    CrossrefPubMed
  • 27 Dubach FF. C, Ellenbroek WG, Storm C. J. Polym. Sci. 2021; 59: 1188
    Crossref
  • 28 Daniele MA, Bandera YP, Foulger SH. Photochem. Photobiol. 2012; 88: 129
    CrossrefPubMed
  • 29 Synthesis of OFP diol 2 Mechanophore precursor 1 (549 mg, 1.6 mmol, 1.00 equiv) and 3-azido-1-propanol (155 μL, 1.68 mmol, 1.05 equiv) were dissolved in a mixture of THF (20 mL) and water (6 mL). Sodium l-ascorbate (317 mg, 1.6 mmol, 1.00 equiv) was added, followed by CuIISO4·5H2O (40 mg, 0.16 mmol, 0.100 equiv). The heterogeneous mixture was stirred vigorously at rt overnight and was afterwards diluted with water (50 mL). THF was removed in vacuo, and the white precipitate was cooled in an ice bath before collection by filtration. After washing the precipitate with cold water (2 ( 25 mL), it was dried in vacuo to yield the triazole mechanophore diol 2 (70% yield) as white solid. 1H NMR (400 MHz, DMSO-d 6): δ = 8.54 (s, 1 H), 7.52 (dd, J = 7.4, 1.2 Hz, 1 H), 7.41 (dd, J = 6.8, 1.9 Hz, 1 H), 7.30 (dd, J = 6.5, 2.0 Hz, 1 H), 7.18 (qt, J = 5.6, 2.6 Hz, 3 H), 7.04 (td, J = 7.6, 1.3 Hz, 1 H), 6.26 (d, J = 7.6 Hz, 1 H), 4.85 (d, J = 3.1 Hz, 1 H), 4.75 (t, J = 5.1 Hz, 1 H), 4.63 (t, J = 7.0 Hz, 2 H), 4.59 (t, J = 5.9 Hz, 1 H), 3.90 (d, J = 8.3 Hz, 1 H), 3.53 (dt, J = 7.6, 6.0 Hz, 2 H), 3.38 (dd, J = 8.3, 3.1 Hz, 1 H), 2.95 (ddt, J = 13.0, 9.2, 4.7 Hz, 2 H), 2.64–2.41 (m, 2 H), 2.12 (p, J = 6.7 Hz, 2 H); see Figure S1. 13C NMR (101 MHz, DMSO-d 6): δ = 175.94, 174.94, 144.29, 143.10, 141.00, 139.27, 138.42, 126.58, 126.56, 126.17, 126.15, 125.93, 124.82, 124.30, 123.80, 123.67, 57.49, 56.34, 49.23, 48.09, 47.50, 46.76, 44.89, 33.10; see Figure S2. ESI+ HRMS: m/z [MH+] calcd: 445.1870; found: 445.1942; see Figure S3.
  • 30 Cravotto G, Gaudino EC, Cintas P. Chem. Soc. Rev. 2013; 42: 7521
    CrossrefPubMed
  • 31 Dawson WR, Windsor MW. J. Phys. Chem. 1968; 72: 3251
    Crossref
  • 32 Ast S, Fischer T, Müller H, Mickler W, Schwichtenberg M, Rurack K, Holdt H.-J. Chem. Eur. J. 2013; 19: 2990
    CrossrefPubMed
  • 33 Stevenson R, De Bo G. J. Am. Chem. Soc. 2017; 139: 16768
    CrossrefPubMed
  • 34 Sato T, Nalepa DE. J. Appl. Polym. Sci. 1978; 22: 865
    Crossref
  • 35 Kryger MJ, Munaretto AM, Moore JS. J. Am. Chem. Soc. 2011; 133: 18992
    CrossrefPubMed
  • 36 Stauch T, Dreuw A. Chem. Sci. 2017; 8: 5567
    CrossrefPubMed
  • 37 Jacobs MJ, Schneider G, Blank KG. Angew. Chem. Int. Ed. 2016; 55: 2899
    CrossrefPubMed