## 2 Materials and Methods
### Synthesis Procedure: Synthesis of Q-DDQ Charge-Transfer Complex  
Quinine (0.33 g, 1 mmol) dissolved in dry acetonitrile (25 mL) was added to a solution of 2,3-dichloro-5,6-discyano-\(p\)-benzoquinone (0.23 g, 1 mmol) in dry acetonitrile (25 mL) and the reaction mixture was stirred at room temperature for 3 h. The obtained reddish solid product was filtered off, washed with acetonitrile, then dried in vacuo to give 0.43 g of red substance. Yield 76%, mp 188 \({}^{\circ}\)C. \({}^{1}\)H NMR (acetone-\(d_{6}\)) \(\delta\): 1.50 (1H, t, \(J\) = 10.0 Hz, H4), 1.91 (1H, dt, \(J\) = 10.0, 3.0, Hz, H5a), 2.56 (1H, sept., \(J\) = 1.5 Hz, H5b), 2.08-2.10 (2H, m, H7a,b), 2.77 (1H, q, \(J\) = 5 Hz, H3), 3.18 (1H, ddd, \(J\) = 10, 5, 1.5 Hz, H6a), 3.27 (1H, dt, \(J\) = 11.5, 3.5 Hz, H6b), 3.58 (1H, t, \(J\) = 9 Hz, H2a), 3.68 (1H, t, \(J\) = 6 Hz, H2b), 4.05 (1H, t, \(J\) = 10 Hz, H8), 4.17 (3H, s OCH\({}_{3}\)), 5.02 (1H, d, \(J\) = 7.5 Hz, H11), 5.14 (1H, \(J\) = 12.5 Hz, H11), 5.85 (1H, ddd, \(J\) = 12.5, 7, 5 Hz, H10), 6.94 (1H, br s OH), 6.55 (1H, dd, \(J\) = 6.5, 1.5 H9), 7.79 (1H, dd, \(J\) = 9, 2 Hz, H7\({}^{\prime}\)), 7.96 (1H, d, \(J\) = 4.0 Hz, H3\({}^{\prime}\)), 8.09 (1H, m, H5\({}^{\prime}\)), 8.32 (1H, dd, \(J\) = 9.5, 4.7 Hz, H8\({}^{\prime}\)), 9.10 (1H, dd, \(J\) = 4.0, 1.0 Hz, H2\({}^{\prime}\)) ppm. \({}^{13}\)C NMR (acetone-\(d_{6}\)) \(\delta\): 174.32 (DDQ), 172.02 (DDQ), 171.09 (DDQ), 161.89 (DDQ), 159.48 (DDQ), 159.45 (6\({}^{\prime}\)), 150.86 (4\({}^{\prime}\)), 144.66 (2\({}^{\prime}\)), 138.95 (10\({}^{\prime}\)), 136.24 (10), 129.24 (8\({}^{\prime}\)), 126.78 (9\({}^{\prime}\)), 119.80 (7\({}^{\prime}\)), 116.33 (3\({}^{\prime}\)), 113.75 (11), 102.88 (5\({}^{\prime}\)), 101.70 (DDQ), 87.82 (DDQ), 65.85 (9), 58.77 (8), 57.68 (2), 53.03 (MeO), 42.71 (6), 40.43 (DDQ), 36.79 (3), 26.67 (4), 23.81 (5), 17.63 (7) ppm. FT-IR (KBr disk) n: 3247 (OH), 2934 (CH\({}_{2}\)), 2209 (CN), 1697 (C=O), 1562 (C=C), 1427 (C=C), 1246 (C=O), 1019 (C=N), 819 cm\({}^{-1}\).  
Synthesis of Q-TCNQ charge-transfer complex Quinine (0.33 g, 1 mmol) and 2,2\({}^{\prime}\)-(cyclohex-2,5-diene-1,4-diylidene) dimalononitrile (0.20 g, 1 mmol) were dissolved in dry acetonitrile and the reaction mixture was stirred at 70 \({}^{\circ}\)C for 3 h. The obtained greenish solid product was filtered off, washed with acetonitrile, then dried in air to give 0.42 g of red substance. Yield 79 %, mp 137 \({}^{\circ}\)C. \({}^{1}\)H NMR (acetone-\(d_{6}\)) \(\delta\): 1.50 (1H, t, \(J\) = 10 Hz, H4), 1.91 (1H, dt, \(J\) = 10, 2 Hz, H5a), 20.8-2.10 (2H, m H7a,b), 2.56 (1H, sept., \(J\) = 1.5 Hz, H5b), 2.08-2.10 (2H, m H7a,b), 2.77 (1H, d\(J\) = 5 Hz, H3), 3.18 (1H, ddd, \(J\) = 10.5, 5, 2 Hz, H6a), 3.27 (1H, dt, \(J\) = 10.5, 3.5 Hz, H6b), 3.58 (1H, ddd, \(J\) = 12.5, 8.5, 7.5 Hz, H2a), 3.68 (1H, ddd, \(J\) = 12.5, 8.5, 7.5 Hz, H2b), 4.05 (1H, d\(J\) = 8.5 Hz, H8), 4.17 (3H, s OCH\({}_{3}\)), 5.02 (1H, d\(J\) = 7.5 Hz, H11), 5.14 (1H, \(J\) = 12 Hz, H11), 5.85 (1H, ddd, \(J\) = 12, 7, 5 Hz, H10), 6.94 (1H, br s OH), 6.55 (1H, d\(J\) = 3 Hz, H9), 7.79 (1H, dd, \(J\) = 6.5, 2 Hz, H7\({}^{\prime}\)), 7.96 (1H, d\(J\) = 2 Hz, H3\({}^{\prime}\)), 8.10 (1H, d\(J\) = 3 Hz, H5\({}^{\prime}\)), 8.32 (1H, d\(J\) = 6.5 Hz, H8\({}^{\prime}\)), 9.10 (1H, d\(J\) = 3.2 Hz, H2\({}^{\prime}\)) ppm. \({}^{13}\)C NMR (acetone-\(d_{6}\)) \(\delta\): 161.94 (TCNQ), 158.06 (6\({}^{\prime}\)), 153.08, (TCNQ), 146.84 (4\({}^{\prime}\)), 146.26 (2\({}^{\prime}\)), 142.94 (10\({}^{\prime}\)), 138.99 (10), 130.66 (8\({}^{\prime}\)), 129.45 (TCNQ), 125.82 (TCNQ), 125.78 (9\({}^{\prime}\)), 124.66 (TCNQ), 124.02 (TCNQ), 122.42 (7\({}^{\prime}\)), 121.11 (TCNQ), 119.15 (3\({}^{\prime}\)), 118.07 (TCNQ), 116.19 (11), 114.53 (TCNQ), 102.10 (TCNQ), 102.03 (5\({}^{\prime}\)), 65.54 (9), 58.99 (8), 57.17 (2), 52.89 (MeO), 42.69 (6), 40.43 (TCNQ), 36.77 (3), 26.72 (4), 25.48 (TCNQ), 23.84 (5), 17.62 (7) ppm. FT-IR (KBr disk): 3247 (OH), 2929 (CH\({}_{2}\)), 2179 (CN), 1620 (C=C), 1508 (C=C), 1433 (C=C), 1241 (C-O), 1025 (C-N), 857, 717 cm\({}^{-1}\).