Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle

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1 Supporting Information Light-Controlled Switching of a Non- Photoresponsive Molecular Shuttle Liu-Pan Yang, a,b Fei Jia, a Jie-Shun Cui, a Song-Bo Lu, a and Wei Jiang* a a Department of Chemistry, South University of Science and Technology of China, Xueyuan Blvd 1088, Nanshan District, Shenzhen, , P. R. China. b Dalian Institute of Chemical Physics, Chinese Academy of Science, Dalian, , P. R. China * Table of Contents 1. Experimental Section S2 2. 2D NMR of Rotaxanes 1a and 1b S10 3. Properties of Rotaxanes 1a and 1b S16 4. Reversibility of 5H + S19 5. Reversibility of the mixture of 1a and 5H + S20 S1

2 1. Experimental Section 1.1 General method All the reagents involved in this research were commercially available and used without further purification unless otherwise noted. Solvents were either employed as purchased or dried prior to use by standard laboratory procedures. 1 H, 13 C, and 1 H- 1 H COSY NMR, 1 H- 1 H ROESY NMR spectra were recorded on Bruker Avance-400, 500 spectrometers. All chemical shifts are reported in ppm with residual solvents or TMS (tetramethylsilane) as the internal standards. The following abbreviations were used for signal multiplicities: s, singlet; d, doublet; t triplet; m, multiplet. Electrospray-ionization time-of-flight high-resolution mass spectrometry (ESI-TOF- HRMS) experiments were conducted on an applied biosystems Elite ESI-QqTOF mass spectrometry system. Photoacid 4, 1 S1 2 and S2 3 were synthesized according to the literature procedures Synthetic Procedures Rotaxanes 1b and 1a DB24C8 (45 mg, 0.10 mmol) and S1 (55 mg, 0.11 mmol) were dissolved in super-dry DCM (2 ml) and stirred for 1 hour at room temperature. S2 (28 mg, 0.11 mmol), Cu(CH 3 CN) 4 PF 6 (75 mg, 0.20 mmol), premixed AcOH (7 µl, 0.12 mmol) and DIPEA (10 µl, 0.06 mmol) in DCM (0.5 ml) were added to the reaction mixture, and 1. Shi, Z.; Peng, P.; Strohecker, D.; Liao, Y. J. Am. Chem. Soc. 2011, 133, Kwan, C.-S.; Chan, A. S. C.; Leung, K. C.-F. Org. Lett. 2016, 18, Gassensmith, J. J.; Barr, L.; Baumes, J. M.; Paek, A.; Nguyen, A.; Smith, B. D. Org. Lett. 2008, 10, S2

3 stirred for 24 hours at ambient temperature under careful Ar protection. After that, CH 3 CN (2 ml) and CH 3 I (0.5 ml) were added. The mixture was stirred and heated at 40 o C for another 24 hours, then the solvent was removed under reduced pressure. The crude product was suspended in acetone (10 ml), a saturated aqueous solution of NH 4 PF 6 was added, and the mixture stirred until the suspension became clear. The solvent was removed and water (20 ml) was added to the residue. The resulting mixture was then filtered, washed with water, and dried. The residue was purified by column chromatography on silica gel (50:1 DCM/MeOH) to afford 1b as a white solid (90 mg, 67%). 1b: 1 H NMR (500 MHz, CDCl 3 ) δ 8.60 (s, 1H), 8.49 (d, J = 8.9 Hz, 2H), 8.19 (s, 1H), 7.88 (d, J = 8.4 Hz, 2H), 7.79 (s, 2H), (m, 3H), (m, 2H), 7.42 (d, J = 8.4 Hz, 2H), 7.36 (d, J = 1.8 Hz, 2H), 7.05 (d, J = 8.3 Hz, 2H), 6.72 (dd, J = 6.1, 3.5 Hz, 4H), 6.41 (dd, J = 6.0, 3.6 Hz, 4H), 5.68 (s, 2H), 5.51 (t, J = 6.4 Hz, 2H), 5.34 (s, 2H), (m, 2H), 4.38 (s, 3H), 3.97 (dd, J = 9.4, 5.5 Hz, 4H), 3.82 (d, J = 9.6 Hz, 8H), 3.68 (dd, J = 10.1, 5.5 Hz, 4H), (m, 8H), 1.34 (s, 18H). 13 C NMR (126 MHz, CDCl 3 ) δ , , , , , , , , , , , , , , , , , , 70.99, 70.37, 68.06, 58.56, 58.45, 52.41, 45.23, 38.80, 35.01, 31.31, ESI- HRMS: m/z calcd for [M-2PF - 6 ] 2+ C 65 H 80 N 4 O 9, ; found , (Error = -1.0 ppm). S3

4 1 H NMR spectrum (500 MHz, CDCl 3, 25 o C) of 1b 13 C NMR spectrum (126 MHz, CDCl 3, 25 o C) of 1b S4

5 ESI mass spectrum of 1b O O O O H O 2 N O N N H O O N N N N O O N NaOH O O O O PF 6 PF 6 PF 6 O O O O 1b 1a After sonicating 1b (50 mg) in 3 ml aqueous solution of NaOH (1.0 M) for 2 hours, 1a was obtained by filtration as a white solid (41 mg, 92%). 1a: 1 H NMR (500 MHz, Acetone-d 6 ) δ 9.71 (s, 1H), 8.53 (s, 1H), (m, 2H), (m, 2H), 7.63 (d, J = 1.9 Hz, 1H), (m, 4H), 7.46 (d, J = 1.8 Hz, 2H), 7.27 (d, J = 8.4 Hz, 2H), 6.97 (dd, J = 6.0, 3.6 Hz, 4H), (m, 6H), 5.76 (s, 2H), 5.64 (s, 2H), 4.64 (s, 2H), 4.37 (s, 3H), (m, 4H), (m, 4H), 3.97 (s, 2H), (m, 4H), 3.65 (m, 4H), 3.46 (m, 4H), 3.34 (dd, J = 10.9, 6.2 Hz, 4H), 1.32 (s, 18H). 13 C NMR (126 MHz, Acetone-d 6 ) δ , , , , , , , , , , , , , , , , , , , , , 70.69, 69.78, 68.08, 59.40, 57.25, 53.31, 44.73, 37.70, 34.66, ESI-HRMS: m/z calcd for [M- PF - 6 +H + ] 2+ C 65 H 80 N 4 O 9, ; found , (Error = -1.3 ppm). S5

6 1 H NMR spectrum (500 MHz, Acetone-d 6, 25 o C) of 1a 13 C NMR spectrum (126 MHz, Acetone-d 6, 25 o C) of 1a S6

7 ESI mass spectrum of 1a Photoacids 5H + S O H N N S I N NH 4 OAc N I 5H HN N The synthesis of 5H + follows the procedure reported by Liao and co-workers. 4 A mixture of 2,3-dimethylbenzo[d]thiazol-3-ium iodide (145 mg, 0.50 mmol), 1-Hindazole-7-carbaldehyde (0.084 g, 0.58 mmol) and ammonium acetate (5 mg) was refluxed in absolute ethanol (2 ml) in dark for 2 h. An orange solid was obtained by filtration, washed with cold ethanol and dried in vacuo (104 mg, 50% yield). 1 H NMR (400 MHz, DMSO-d 6 ) δ (s, 1H), 8.60 (d, J = 15.8 Hz, 1H), 8.48 (d, J = 8.1 Hz, 1H), (m, 3H), (m, 2H), 7.87 (dt, J = 31.7, 7.6 Hz, 2H), 7.35 (t, J = 7.7 Hz, 1H), 4.25 (s, 3H). 13 C NMR (126 MHz, DMSO-d 6 ) δ , , , , , , , , , , , 4. Abeyrathna, N.; Liao, Y. J. Am. Chem. Soc. 2015, 137, S7

8 121.55, , , , HRMS (ESI): m/z [M-I] + Calcd for C 17 H 14 N 3 S , found H NMR spectrum (500 MHz, DMSO-d 6, 25 o C) of 5H + 13 C NMR spectrum (126 MHz, DMSO-d 6, 25 o C) of 5H + S8

9 ESI mass spectrum of 5H + S9

10 2. 2D NMR of rotaxane Figure S1. Partial 1 H, 1 H-COSY NMR spectrum (500 MHz, acetone-d 6, 6.0 mm, 298 K) of rotaxane 1a. S10

11 Figure S2. Partial 1 H, 1 H-ROESY NMR spectrum (500 MHz, acetone-d 6, 6.0 mm, 298 K) of rotaxane 1a. S11

12 Figure S3. Partial 1 H, 1 H-COSY NMR spectrum (500 MHz, acetone-d 6, 6.0 mm, 298 K) of rotaxane 1b. S12

13 Figure S4. Partial 1 H, 1 H-ROESY NMR spectrum (500 MHz, acetone-d 6, 6.0 mm, 298 K) of rotaxane 1b. S13

14 Figure S5. Partial 1 H, 1 H-COSY NMR spectrum (500 MHz, DMSO-d 6, 6.0 mm, 298 K) of rotaxane 1b. S14

15 Figure S6. Partial 1 H, 1 H-ROESY NMR spectrum (500 MHz, DMSO-d 6, 6.0 mm, 298 K) of rotaxane 1b. S15

16 3. Properties of Rotaxanes 1a and 1b Figure S7. Partial 1 H NMR spectra (500 MHz, 25 C) of rotaxanes 1b and 1a in acetone-d 6 or DMSO-d 6. The key peaks in both solvents are rather similar for 1a and 1b, respectively. This supports that the location of the wheel on the axle is not affected by solvents but is decided by the protonation state of the secondary amine of the axle. S16

17 Figure S8. Partial 1 H NMR spectra (500 MHz, 1.0 mm, 25 C) of 1a in different deuterated solvent. Figure S9. Partial 1 H NMR spectra (500 MHz, DCM-d 2, 1.0 mm, 25 C) of 1a (bottom) and 1b (top). S17

18 Figure S10. Partial 1 H NMR spectra (500 MHz, tol-d 8, 1.0 mm, 25 C) of 1a (bottom) and 1b (top). Figure S11. Fluorescence spectra of 1a (λ ex = 365 nm, M) in dry toluene when titrating with water (toluene:water: 100:1, 100:2; v/v). This indicates that the presence of water has no obvious effect on fluorescent property of 1a. S18

19 4. Properties of 5H + Figure S12. 1 H NMR spectrum of 5H + before irradiation (Only the aromatic part is shown for viewing clarity.) Figure S13 1 H NMR spectra of 5H + after irradiation (top: 10 min, blue light (413 nm). middle: 30 min, 365 nm ultraviolet lamp, bottom: stayed in dark over night after irradiation by a 365 nm ultraviolet lamp) showed a mixture of the photoproduct PA, cis-5h + and trans-5h + due to the reverse reaction, 4 blue light (413 nm) is more efficient for the formation of 5, and only a little 5 exist after staying in dark over night after irradiation by a 365 nm ultraviolet lamp. S19

20 5. Reversibility of the mixture of 1a and 5H + Figure S14. 1 H NMR spectra (500 MHz, DMSO-d 6, 25 C) variations of a mixture of rotaxane 1a and a mixture of 1a and 5H + before and after irradiation by a 365 nm ultraviolet lamp. S20

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