## 2 Materials and Methods
### Chemistry
#### 2.2.3 Compound Data  
_(E)-N-(1H-benzimidazole-2-yl)-1-(thiophene-2-yl)methanimine_ (**4a**):  
mp 224-225 \({}^{\circ}\)C, Rf = 0.539, IR (KBr) v/ cm\({}^{-1}\): 3410, 3100, 3232, 1582, 1045, 740. \({}^{1}\)H NMR (400 MHz, DMSO-d6): 12.67 (br s, 1H, NH), 9.58 (s, 1H, N=CH), 7.98 (m, 2H), 7.49 (d,2H, J = 51.63 Hz,,), 7.31 (t, 1H, J = 4.48 Hz), 7.17 (m, 2H). \({}^{13}\)C NMR (150 MHz, DMSO-d6) \(\delta\) (ppm): 158.6, 155.9, 141.8, 137.3, 133.9, 129.3, 128.7, 122.3, 118.8. HRMS (ESI) m/z: Calcd. for: C\({}_{12}\)H\({}_{3}\)N\({}_{3}\)S: 227.0523; Found: 228.0585 [M + H]\({}^{+}\). Anal. Calcd. for C\({}_{12}\)H\({}_{3}\)N\({}_{3}\)S: C, 63.41; H, 3.99; N, 18.49; Found: C, 62.91; H, 4.39; N, 18.19.  
_(E)-N-(1-methyl-1H-benzimidazole-2-yl)-1-(thiophen-2-yl)methanimine_ (**4b**): mp 115-117 \({}^{\circ}\)C, Rf = 0.584; IR (KBr) \(\upsilon\)/ cm\({}^{-1}\): 3096, 1616, 1045, 735,\({}^{1}\)H NMR (400 MHz, DMSO-d6): 9.54 (s, 1H, N-CH), 7.20-7.70 (m, 4H), 6.90-6.83 (bd, 2H), 3.64 (s, 3H). HRMS (ESI) m/z: Calcd. for: C\({}_{13}\)H\({}_{11}\)N\({}_{3}\)S: 241.0779; Found: 242.0742 [M + H]\({}^{+}\). Anal. Calcd. for C\({}_{13}\)H\({}_{11}\)N\({}_{3}\)S: C, 64.71; H, 4.59; N, 17.41; Found: C, 64.61; H, 4.83; N, 17.46.  
_(E)-N-(1-ethyl-1H-benzimidazole-2-yl)-1-(thiophen-2-yl)methanimine_ (**4c**): mp 104-105 \({}^{\circ}\)C, Rf = 0.563; IR (KBr) \(\upsilon\)/ cm\({}^{-1}\): 3064, 1615, 1046, 734. \({}^{1}\)H NMR (400 MHz, 400 MHz, DMSO-d6): 9.60 (d, 1H, J = 0.80 Hz), 7.99 (m, 2H), 7.57 (m, 2H), 7.32 (m, 1H), 7.22 (m, 2H), 4.37 (q, 2H, J = 7.11 Hz), 135 (t, 3H, J = 7.14 Hz). \({}^{13}\)C NMR (150 MHz, DMSO-d6) \(\delta\) (ppm): 158.6, 154.5, 142.0, 141.8, 137.5, 134.8, 134.3, 129.4, 122.6, 122.4, 119.17, 110.6, 37.6, 15.5. HRMS (ESI) m/z: Calcd. for C\({}_{14}\)H\({}_{13}\)N\({}_{3}\)S: 255.0836; Found: 256.0896 [M + H]\({}^{+}\). Anal. Calcd. for C\({}_{14}\)H\({}_{13}\)N\({}_{3}\)S: C, 65.86; H, 5.13; N, 16.46; Found: C, 65.62; H, 5.35; N, 16.22.  
_(E)-2-(2-(thiophen-2-ylmethylylene)hydrazinyl)-1H-benzimidazole_ (**6a**): mp 267-268 \({}^{\circ}\)C, Rf = 0.563; \({}^{1}\)H NMR (400 MHz, DMSO-d6): 11.32 (bs, 1H, NH), 8.25 (s, 1H), 7.57 (m, 2H), 7.57 (dt, 1H, J = 0.99 Hz, J = 4.99 Hz), 7.34 (dd, 1H, J = 0.43 Hz, J = 3.59 Hz), 7.22 (m, 2H), 7.10 (dd, 1H, J = 3.58 Hz, J = 4.94 Hz), 6.95 (m, 2H). \({}^{13}\)C NMR (150 MHz, DMSO-d6) \(\delta\) (ppm): 153.6, 140.3, 137.1, 128.7, 128.1, 127.5. HRMS (ESI) m/z: Calcd. for C\({}_{12}\)H\({}_{10}\)N\({}_{4}\)S: 242.0632; Found: 243.0694 [M + H]\({}^{+}\). Anal. Calcd. for C\({}_{12}\)H\({}_{10}\)N\({}_{4}\)S: C, 59.48; H, 4.16; N, 23.12; Found: C, 59.63; H, 3.80; N, 23.26.  
_(E)-2-(2-(furan-2-ylmethylylene)hydrazinyl)-1H-benzimidazole_ (**6b**): mp 230-231 \({}^{\circ}\)C, Rf = 0.620; IR (KBr) \(\upsilon\)/ cm\({}^{-1}\):1653, 1239, 1010, 730. \({}^{1}\)H NMR (400 MHz, DMSO-d6): 11.40 (bs, 1H, NH), 7.96 (s, 1H), 7.78 (dd, 1H, J = 0.68 Hz, J = 1.91 Hz), 7.22 (t, 2H, J = 4.47 Hz), 6.95 (m, 2H) 6.80 (dd, 1H, J = 0.34 Hz, J = 1.75 Hz), 6.62 (dd, 1H, J = 1.89 Hz, J = 3.33 Hz). HRMS (ESI) m/z: Calcd. for C\({}_{12}\)H\({}_{10}\)N\({}_{4}\)O: 226.0860; Found: 227.0922 [M + H]\({}^{+}\). Anal. Calcd. for C\({}_{12}\)H\({}_{10}\)N\({}_{4}\)O: C, 63.71; H, 4.46; N, 24.76, Found: C, 63.35; H, 4.21; N, 24.95.  
_(E)-2-(2-(pyridin-4-ylmethylylene)hydrazinyl)-1H-benzimidazole_ (**6c**): mp 294-295 \({}^{\circ}\)C, Rf = 0.500; IR (KBr) \(\upsilon\)/ cm\({}^{-1}\): 3056, 1637, 812, 721. \({}^{1}\)H NMR (400 MHz, DMSO-d6): 11.72 (bs, 1H, NH), 8.59 (dd, 2H, J = 1.63 Hz, J = 4.36 Hz),7.99 (s, 1H), 7.76 (dd, 2H, J = 1.54 Hz, J = 4.43 Hz), 7.26 (m, 2H),7.00 (m, 2H). HRMS (ESI) m/z: Calcd. for C\({}_{13}\)H\({}_{11}\)N\({}_{5}\): 237.1020; Found: 238.1083 [M + H]\({}^{+}\). Anal. Calcd. for C\({}_{13}\)H\({}_{11}\)N\({}_{5}\): C, 65.81; H, 4.67; N, 29.52, Found: C, 65.45; H, 4.34; N, 29.72.