Compound 2

4-cyano-2-(2,6-dimethylphenyl)-1,1-difluoro-1,2-dihydropyrido[1,2-d][1,2,4,3]triazaborinin-9-ium-1-uide

From: Suppression of Kasha's rule as a mechanism for fluorescent molecular rotors and aggregation-induced emission

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Compound data: CIF

Compound data: FCF

Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.

Hydrazone 2: the compound was synthesized following the procedure used for Hydrazone 1, while using 2,6-dimethylaniline as the substituted aniline. Hydrazone 2 was obtained as a yellow crystalline powder; yield 63%. m.p. 132.3 – 132.8 oC; 1H NMR (500 MHz, CDCl3) δ 14.87 (s, 1H), 8.60 (d, J = 5.0 Hz, 1H), 7.91 (td, J = 8.2, 7.6 Hz, 1H), 7.76 (d, J = 8.2 Hz, 1H), 7.32 (dd, J = 7.5, 5.0 Hz, 1H), 7.10 – 7.06 (m, 2H), 7.00 (dd, J = 8.1, 6.9 Hz, 1H), 2.46 (s, 6H) ppm. 13C NMR (126 MHz, CDCl3) δ 152.66, 147.16, 139.17, 137.89, 129.68, 129.22, 125.20, 122.66, 121.81, 118.03, 110.49, 19.74 ppm; GC-MS: calcd for C15H14N4 250.12; m/z (rel. inten.) 250.10 (27%, M+), 144.20 (24%), 118.15 (58 %), 105.15 (100%), 90.10 (73%).

2: the compound was synthesized following the procedure used for 1, while starting from Hydrazone 2. The compound was obtained as a light yellow crystalline powder; yield 41%. m.p. 176.0 – 176.6 oC; 1H NMR (500 MHz, CDCl3) δ 8.64 (d, J = 5.9 Hz, 1H), 8.26 (t, J = 7.9 Hz, 1H), 7.95 (d, J = 8.4 Hz, 1H), 7.66 (t, J = 7.2 Hz, 1H), 7.28 – 7.09 (m, 3H), 2.21 (s, 6H) ppm; 13C NMR (126 MHz, CDCl3) δ 143.20, 142.06, 141.65, 139.87, 136.29, 128.83, 128.69, 123.96, 120.82, 115.45, 18.19, 18.17, 18.15 ppm; 19F NMR (470 MHz, CDCl3) δ -137.86 (dd, J = 56.9, 27.3 Hz, 2F) ppm; GC-MS: calcd for C15H14N4 298.12; m/z (rel. inten.) 298.10 (45%, M+), 181.05 (32%), 167.10 (43%), 118.10 (100%).

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