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DOI: 10.1016/j.mencom.

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Reagents and conditions: i, glyoxal, Na2SO4, CH2Cl2, 0 °C; ii, (COD)Pd(Me)Cl, CH2Cl2, room temperature.

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(a) Normalized (1) emission and (2) excitation spectra of solid 1·CH2Cl2 at 298 K. (b) Temperature-dependent emission spectra ( λex = 320 nm) of solid 1·CH2Cl2 recorded at (1) 77, (2) 100, (3) 125, (4 ) 150, (5) 175, (6) 200, (7) 225, (8) 250, (9) 275 and (10) 300 K. See Guidelines for Illustrations.

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Solid-state structure of complex 7∙PhMe shown (a) from the front and (b) from the side. Ellipsoids are shown at the 50% probability level; co-crystallized hexane and hydrogen atoms are omitted for clarity. For selected bond lengths and angles, see Online Supplementary Materials. See Guidelines for Illustrations.

Reagents and conditions: i, bromide 1, AgOTf, TMU, CH2Cl2, room temperature, 20 h; ii, 80% aq. AcOH, 70 °C, 2 h, then Ac2O/Py; iii, 0.1 M MeONa/MeOH, 30 min, then 0.1 M aq. NaOH.

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Entrya	Sample	C/mol dm–3	a/Åb	a/deg	T/°C	t/minb
1	Compounda	10.5	10.02	15	100	1
2	Compound	0.2с	12.42	18	120	5
3	Compound	0.8	16.69	25	150	10
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Online Supplementary Materials

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References

A. V. Kucherov, Mendeleev Commun., 2016, 26, 254.

V. A. Golubev and V. D. Sen’, Russ. J. Org. Chem., 2013, 49, 555 (Zh. Org. Khim., 2013, 49, 572).

J. M. Thomas and W. J. Thomas, Principles and Practice of Heterogeneous Catalysis, 2nd edn., Wiley-VCH, Weinheim, 2014.

Fluorine in Heterocyclic Chemistry, ed. V. G. Nenajdenko, Springer, Berlin, 2014.

G. N. Nikonov and S. Bobrov, in Comprehensive Heterocyclic Chemistry, eds. A. R. Katritzky, C. A. Ramsden, E. F. V. Scriven and R. J. K. Taylor, Elsevier, Amsterdam, 2008, vol. 5, pp. 316–393.

B. A. Trofimov, A. I. Mikhaleva, E. Yu. Schmidt and L. N. Sobenina, Khimiya pirrola. Novye stranitsy (Chemistry of Pyrrole. New Pages), Nauka, Novosibirsk, 2012 (in Russian).

S. A. Chesnokov, S. N. Mensov, G. A. Abakumov, R. S. Kovylin, M. A. Baten’kin, A. N. Konev and Yu. V. Chechet, RU Patent 2525908, 2013.

M. A. Smirnov, A. S. Mukhtarov, N. V. Ivanova, T. A. Vakhonina, V. V. Bazarov and M. Yu. Balakina, XIX International Youth Scientific School ‘Coherent Optics and Optical Spectroscopy’, Kazan, 2015, p. 182.

[dataset] A. A. Granovsky, Firefly computational chemistry program, version 8.0.1, 2014.http://classic.chem.msu.su/gran/gamess/index.html

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Crystal data for 5f. C5H5N6F3O4 (M = 270.13), monoclinic, space group P21/n, a = 11.430(12), b = 5.630(7) and c = 15.64(2) Å, β = 103.10(10)°, V = 980(2) Å3, μ(MoKα) = 1.714 mm–1. Analysis was performed at 295(2) K on an Xcalibur 3 diffractometer by standard procedure (graphite monochromated MoKα radiation, ω-scanning). On the angles 4.36<θ<65.23° total of 7324 reflections were measured, 1660 unique reflections (Rint = 0.0390), 1507 reflections with I > 2σ(I). The structure was solved and refined using the SHELXTL program package. The structure was defined by direct statistical methods and refined by full-matrix anisotropic approximation for F2 for all non-hydrogen atoms with ShelXL program. The hydrogen atoms were localized by direct method and refined in the isotropic approximation. GOOF = 1.007, S = 1.038; final R values: R1 = 0.0443, wR2 = 0.1361 [I > 2σ(I)]; R1 = 0.0476, wR2 = 0.1396 (all data). Residual electronic density max/min was 0.312/ –0.247 eÅ–3.

CCDC 1529899 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via http://www.ccdc.cam.ac.uk.