SUPPORTING INFORMATION. Visible Light Excitation of a Molecular Motor with an Extended Aromatic Core
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- Αἴσωπος Κούνδουρος
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1 SUPPORTING INFORMATION Visible Light Excitation of a Molecular Motor with an Extended Aromatic Core Thomas van Leeuwen, Jasper Pol, Diederik Roke, Sander J. Wezenberg, Ben L. Feringa* Stratingh Institute for Chemistry, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands. b.l.feringa@rug.nl Table of Contents General Remarks... S2 NMR spectra... S4 HRMS spectra... S8 Eyring Plot... S10 Computational Details... S11 References... S21 S1
2 General Remarks Compounds 4 and 6 were synthesized following procedures that are described in the literature. 1,2 All other reagents were obtained from commercial sources and used as received without further purification. Dry solvents were obtained from a MBraun solvent purification system. Column chromatography was performed on a Reveleris X2 Flash Chromatography system, TLC: silica gel 60, Merck, 0.25 mm. High Resolution Mass spectra (HRMS) were recorded on an LTQ Orbitrap XL. NMR spectra were obtained using a Varian Mercury Plus ( 1 H, 400 MHz, 13 C, 100 MHz), or a Varian Innova ( 1 H: 600 MHz) instrument in CDCl 3, or CD 2 Cl 2. Chemical shifts are reported in δ units (ppm) relative to the residual solvent signal of CDCl 3 ( 1 H-NMR, δ 7.26 ppm; 13 C-NMR, δ 77.0 ppm) or CD 2 Cl 2 ( 1 H-NMR, δ 5.32 ppm; 13 C- NMR, δ 54.0 ppm). For 1 H NMR spectroscopy, the splitting pattern of peaks is designated as follows: s (singlet), d (doublet), t (triplet), (multiplet), br (broad), p (quintet) or dd (doublet of doublets). UV-vis absorption spectra were measured on a Hewlett-Packard 8453 spectrometer diode array spectrometer in a 1 cm quartz cuvette. Dichloromethane used for spectroscopic studies was of spectroscopic grade (UVASOL, Merck). Irradiation experiments were performed using Thorlab LEDs. Density functional theory (DFT) calculations were carried out with the Gaussian 09 program (rev. D.01) program package. 3 All of the calculations were performed on systems in the gas phase using the Becke s three parameter hybrid functional 4 with the LYP correlation functional 5,6 (DFT B3LYP/6-31G(d,p)). Each geometry optimization was followed by a vibrational analysis to determine that a minimum or saddle point on the potential energy surface was found. (7H-dibenzo[c,g]fluoren-7-ylidene)hydrazine (5) Hydrazine monohydrate (2 ml) was added to a solution of ketone 4 (0.30 g, 1.07 mmol) in EtOH (50 ml) and the solution was heated at reflux for 3 h. The reaction mixture was poured onto water and extracted with CH 2 Cl 2 (2 x 50 ml). The organic layer was dried over Na 2 SO 4 and concentrated in vacuo. The crude compound was purified by column chromatography (SiO 2, pentane: ethyl acetate = 5: 1). Hydrazone 5 was obtained as an orange crystalline solid (0.20 g, 0.68 mmol, 64 %). 1 H-NMR (400 MHz, CDCl 3 ): δ(ppm) (m, 1H), 8.51 (d, J = 8.1 Hz, 1H), 8.09 (d, J = 8.4 Hz, 1H), (m, 5H), (m, 4H). 13 C- NMR: δ(ppm) 145.1, 140.2, 137.3, 135.7, 135.1, 134.9, 129.0, 128.7, 128.5, 128.4, 128.3, 128.2, 127.9, 127.7, 126.8, 126.4, 125.5, 125.3, 125.1, 121.8, HRMS (ESI) m/z: [M + H] + Calcd for C 21 H 15 N ; Found S2
3 7-(2-methyl-2,3-dihydro-1H-cyclopenta[a]naphthalen-1-ylidene)-7H-dibenzo[c,g]fluorene (2) Activated MnO 2 (0.20 g, 2.30 mmol) was added to a stirred solution of 5 (0.20 g, 0.68 mmol) in dry THF (5 ml). The mixture was stirred for 15 min and filtered over a plug of celite. The obtained diazo solution was added dropwise to solution of 6 (0.17 g, 0.80 mmol) in toluene (5 ml). The reaction mixture was stirred at room temperature for 16 h and subsequently concentrated in vacuo. After evaporation of the solvent the crude product was purified by column chromatography (SiO 2, pentane: CH 2 Cl 2 = 5: 1), followed by recrystallization (ethanol: heptane = 1:1), to give alkene 2 as an orange solid (53 mg, 0.12 mmol, 18%). 1 H- NMR (400 MHz, CDCl 3 ): δ(ppm) 8.68 (d, J = 7.4 Hz, 1H), 8.64 (d, J = 8.4 Hz, 1H), (m, 7H), 7.92 (d, J = 8.5 Hz, 1H), 7.78 (d, J = 8.2 Hz, 1H), 7.63 (d, J = 8.2 Hz, 1H), (m, 12H), (m, 3H), 7.05 (d, J = 8.6 Hz, 1H), 4.52 (p, J = 6.5 Hz, 1H), 3.65 (dd, J = 14.9, 5.6 Hz, 1H), 2.86 (d, J = 14.9 Hz, 1H), 1.46 (d, J = 6.7 Hz, 4H). 13 C-NMR (100 MHz, CDCl 3 ): δ(ppm) 154.5, 148.3, 139.2, 137.5, 136.9, 136.5, 136.4, 133.9, 133.8, 132.7, 132.1, 131.4, 130.4, 128.7, 128.6, 128.4, 128.3, 128.3, 127.4, 127.3, 127.1, 126.9, 126.2, 125.5, 125.2, 125.0, 124.8, 124.6, 124.0, 123.5, 121.7, 46.1, 42.3, HRMS(APCI) m/z: [M + H] + Calcd for C 35 H ; Found S3
4 NMR spectra Figure S1: 1 H-NMR of 5 Figure S2: 13 C-NMR of 5 S4
5 Figure S3: 1 H-NMR of 2 Figure S4: 13 C-NMR of 2 S5
6 H c H b H b H a H c H b H b H a Figure S5: 1 H-NMR of 2 in CD 2 Cl 2 upon irradiation. Initial state (bottom spectrum), PSS (top spectrum). NMR irradiation experiments were performed at 40 C with a Thorlab model M420F2 high-power LED coupled to a 600 mm optical fiber, which guided the light into the NMR tube inside the spectrometer. 7 S6
7 Figure S6: Plot of concentration of metastable 1 and 2 versus irradiation time, as determined by UV/Vis spectroscopy (Toluene, -5 C, Abs 420 >2) using the same light-source (Thorlab model M420F2 high-power LED) and setup (= equal photon flux for both experiments). It can be concluded that the photochemical efficiency for the conversion of the stable to the metastable form is lower for 2 than for 1. However, since the PSS ratio for 2 remains in favour of the metastable isomer, the photoconversion efficiency of the backward isomerization process is also significantly lower and the switching function is thus retained. S7
8 HRMS spectra Relative Abundance NL: 5.34E6 JP_03#6-22 RT: AV: 17 T: FTMS + p ESI Full ms [ ] NL: 7.91E5 C 21 H 15 N 2: C 21 H 15 N 2 pa Chrg m/z Figure S7: HRMS of 5 (top: measured, bottom: calcd.) Relative Abundance NL: 4.43E6 JP_009#6-14 RT: AV: 9 T: FTMS + p APCI corona Full ms [ ] NL: 6.84E5 C 35 H 25: C 35 H 25 pa Chrg m/z Figure S8: HRMS of 2 (top: measured, bottom: calcd.) S8
9 Relative Abundance NL: 1.47E5 JP_009#6-14 RT: AV: 9 T: FTMS + p APCI corona Full ms [ ] NL: 6.84E5 C 35 H 25: C 35 H 25 pa Chrg m/z Figure S9: HRMS of 2 (top: measured, bottom: calcd.) S9
10 Eyring Plot Figure S10: Eyring Plot of the THI of 2. A solution of 2 in CH 2 Cl 2 (~1 x 10-5 M) in a 1cm cuvette was irradiated to PSS at 420 nm. The rate of the thermal relaxation was followed by monitoring the absorbance at 475 nm at 6 different temperatures (10, 15, 20, 25, 30, 35 C). The Eyring equation gave the thermodynamic parameters of the process. S10
11 Computational Details Figure S11: DFT optimized structures of TS1 (top left), TS2 (top right), TS3 (bottom left) and TS4 (bottom right) S11
12 SCF energy in Hartree, number of imaginary frequencies and Cartesian coordinates in Ångströms. (P,M) C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H S12
13 H H H H H H H H H H H H H (M,M) C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C H S13
14 H H H H H H H H H H H H H H H H H H H H H H H (P,P) C C C C C C C C C C C C C C C C C C C C C C C C C C S14
15 C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H (M,P) C C C C C C C C C C C C C C C C S15
16 C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H TS C C C C C C S16
17 C C C C C C C C C C C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H H H H H H H H H H S17
18 TS C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C H H H H H H H H H H H H H H H S18
19 H H H H H H H H H TS C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C H H H H H S19
20 H H H H H H H H H H H H H H H H H H H TS C C C C C C C C C C C C C C C C C C C C C C C C C C C C C C S20
21 C C C C C H H H H H H H H H H H H H H H H H H H H H H H H References (1) Tian, Y.; Uchida, K.; Kurata, H.; Hirao, Y.; Nishiuchi, T.; Kubo, T. J. Am. Chem. Soc. 2014, 136, (2) Pijper, D.; Feringa, B. L. Angew. Chem. Int. Ed. 2007, 46, (3) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., J.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01, (4) Becke, A. D. J. Chem. Phys. 1993, 98, 5648 S21
22 (5) Vosko, S. H.; Wilk, L.; Nusair, M. Can. J. Phys. 1980, 58, (6) Lee, C.; Yang, W.; Parr, R. G. Phys. Rev. B 1988, 37, 785. (7) Feldmeier, C.; Bartling, H.; Riedle, E. Gschwind, R. M. J. Magn. Reson. 2013, 232, 39. S22
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