Full Paper
doi.org/10.1002/chem.202100594
Chemistry—A European Journal
[8] A. Członkowska, T. Litwin, P. Dusek, P. Ferenci, S. Lutsenko, V. Medici,
J. K. Rybakowski, K. H. Weiss, M. L. Schilsky, Nat. Rev. Dis. Prim. 2018, 4,
mixture was stirred at room temperature for 20 h. The solvent was
removed, and the residue was dissolved in CH2Cl2 and water. The
organic phase was washed with brine and the combined aqueous
solutions extracted with CH2Cl2. The combined organic phases were
dried over magnesium sulphate and concentrated under reduced
pressure. The crude product was purified by column chromatog-
raphy (eluent CyH/EtOAc, 1:1! 0:1, v/v). After evaporation of the
solvent, product 3 was obtained as a yellowish solid. Yield: 0.6 g
[9] P. P. Leal, C. L. Hurd, S. G. Sander, E. Armstrong, P. A. Fernández, T. J.
Suhrhoff, M. Y. Roleda, Sci. Rep. 2018, 8, 14763.
°
[12] H. Küpper, Lead: Its Effects on Environment and Health, Metal Ions in Life
Sciences, Vol. 17 (Eds.: A. Sigel, H. Sigel, R. K. O. Sigel), Walter de Gruyter,
Berlin, 2017, pp. 491–500.
[14] M. Sakamoto, T. Itai, K. Marumoto, M. Marumoto, H. Kodamatani, T.
Tomiyasu, H. Nagasaka, K. Mori, A. J. Poulain, J. L. Domingo, M. Horvat,
[17] P. Gottesfeld, Public Health 2015, 3, 144.
[18] European Food Safety Authority, Scientific Opinion on Lead in Food.
EFSA J. 2010, 8, 1570.
[19] V. Merz, J. Lenhart, Y. Vonhausen, M. E. Ortiz-Soto, J. Seibel, A. Krueger,
[20] a) A. Gładysiak, T. N. Nguyen, R. Bounds, A. Zacharia, G. Itskos, J. A.
Reimer, K. C. Stylianou, Chem. Sci. 2019, 10, 6140–6148; b) A. Ruiu, M.
Vonlanthen, E. G. Morales-Espinoza, S. M. Rojas-Montoya, I. González-
[21] a) T. Delgado, M. Meneses-Sánchez, L. Piñeiro-López, C. Bartual-Murgui,
S. Shyamsivappan, T. Suresh, G. Subashini, K. Kadirvelu, N. Bhuvanesh, R.
[22] C. S. de Castro, T. F. G. G. Cova, A. C. C. Pais, D. Pinheiro, C. Nuñez, C.
[24] C.-B. Bai, P. Xu, J. Zhang, R. Qiao, M.-Y. Chen, M.-Y. Mei, B. Wei, C. Wang,
[26] J. K. Choi, S. H. Kim, J. Yoon, K.-H. Lee, R. A. Bartsch, J. S. Kim, J. Org.
(0.51 mmol, 32%). M.p.: 180–220 C. Rf (cyclohexane/EtOAc, 1:1):
1
0.05. H NMR (400 MHz, CDCl3): δ=8.94 (s, 3H, H-12), 8.73 (s, 6H, H-
3
7), 8.16 (d, J2,1 =7.6 Hz, 6H, H-2), 8.13–8.03 (m, 12H, H-4+5), 7.99
(dd, 3J1,2 =7.6 Hz, 3H, H-1), 4.81 (br, 1H, H-24), 4.69 (s, 6H, H-13),
3.90–3.81 (m, 4H, H-18/19/20/21), 3.79–3.74 (m, 2H, H-18/19/20/21),
3.74–3.64 (m, 2H, H-18/19/20/21), 3.42–3.33 (m, 2H, H-16), 3.32–3.27
(m, 2H, H-17), 3.27 3.19 (m, 2H, H-22), 3.18–3.01 (m, 4H, H-15+23),
1.36 (s, 9H, H-27) ppm. 13C NMR (100 MHz, CDCl3): δ=156.0 (Cq, C-
25), 148.2 (Cq, C-11), 131.8 (Cq, C-8), 131.2 (Cq, C-6), 128.1 (CH, C-4),
127.9 (Cq, C-3), 127.5 (CH, C-5), 126.2 (CH, C-1), 125.4 (CH, C-2),
124.7 (Cq, C 9/10), 124.6 (Cq, C 9/10), 124.2 (CH, C-12), 122.1 (CH, C
7), 79.3 (Cq, C 26), 77.4 (CH, C-16), 70.8 (CH2, C 17–22), 70.7 (CH2, C
17–22), 70.6 (CH2, C 17–22), 70.5 (CH2, C-17–22), 70.1 (CH2, C 17–22),
70.0 (CH2, C 17–22), 68.3 (CH2, C-15), 49.7 (CH2, C-13), 46.5 (Cq, C-14),
~
40.2 (CH2, C-23), 28. 5 (CH3, C-27) ppm. FT-IR (ATR): v=3127 (w),
3039 (w), 2966 (w), 2868 (m), 1704 (vs), 1608 (m), 1504 (s), 1437 (s),
1365 (s), 1275 (m), 1245 (vs), 1170 (vs), 1137 (vs), 1095 (vs), 1040
(vs), 1006 (w), 962 (vw), 879 (vs), 839 (vs), 819 (vs), 759 (m), 727 (s),
706 (vs), 660 (m), 608 (w) cmÀ 1. HRMS (ESI,+): found: 1164.5000
[M]+; calc. for [M]+: 1164.5010.
Acknowledgements
The authors thank the Volkswagen Foundation for grant
number 88393, the Federal State of Bavaria (project “Solar
Technology Goes Hybrid“) and Deutsche Forschungsgemein-
schaft (MA 4771/8-1) for the financial support of this research.
Open access funding enabled and organized by Projekt DEAL.
[30] A. G. Crawford, A. D. Dwyer, Z. Liu, A. Steffen, A. Beeby, L.-O. Pålsson,
[31] D. N. Coventry, A. S. Batsanov, A. E. Goeta, J. A. K. Howard, T. B. Marder,
[32] B. Valeur, Molecular Fluorescence, 1st ed. Wiley-VCH, Weinheim, 2001.
Conflict of Interest
The authors declare no conflict of interest.
Keywords: Fluorescence spectroscopy
luminescence · probes · pyrene
·
heavy metals
·
[37] a) J. Rodríguez-Lavado, A. Lorente, E. Flores, A. Ochoa, F. Godoy, P.
[41] J. S. Kim, M. G. Choi, K. C. Song, K. T. No, S. Ahn, S.-K. Chang, Org. Lett.
[42] J. B. Birks, D. J. Dyson, I. H. Munro, Proc. R. Soc. London Ser. A 1963, 275,
575–588.
[43] N. P. E. Barry, B. Therrien, Organic Nanoreactors: From Molecular to
Supramolecular Organic Compounds (Ed.: S. Sadjadi), Academic Press
(Elsevier), London, 2016, pp. 421–461.
[1] H. B. Bradl, Heavy Metals in the Environment: Origin, Interaction and
Remediation, Interface Science and Technology 6, Elsevier/Acad. Press,
Amsterdam, 2005.
[4] K. K. Kesari, Ed., Networking of Mutagens in Environmental Toxicology,
Environmental Science and Engineering, Environmental Science, Spring-
er, Cham 2019.
[6] a) L. Ma, Q. Wang, S. M. Islam, Y. Liu, S. Ma, M. G. Kanatzidis, J. Am.
Patlolla, D. J. Sutton, Molecular, Clinical and Environmental Toxicology.
Experientia Suppl. Vol. 101 (Ed.: A Luch), Springer, Basel, 2012, pp.133–
164.
[44] A. G. Crawford, Z. Liu, I. A. I. Mkhalid, M.-H. Thibault, N. Schwarz, G.
Alcaraz, A. Steffen, J. C. Collings, A. S. Batsanov, J. A. K. Howard, T. B.
[7] M. Jaishankar, T. Tseten, N. Anbalagan, B. B. Mathew, K. N. Beeregowda,
Chem. Eur. J. 2021, 27, 1–10
8
© 2021 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH
��
These are not the final page numbers!