Yield: 88%; m.p. 195-196 °C; as a pale pinkish solid; IR (KBr, cm-1): 3098, 2834, 1600, 1550, 1448, 1342,
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1172, 861, 771, 680; (closed-form, 67%): H NMR (400 MHz, CDCl3): δ 2.69 (s, 1H, H-6), 3.69 (s, 1H, H-5),
3.89 (s, 3H, OCH3), 3.92 (s, 3H, OCH3,), 6.77 (s, 1H, H-2), 6.96-7.05 (m, 4H), 7.28 (m, 1H), 7.35 (d, J = 8.4
Hz, 2H), 7.44-7.47 (m, 2H), 7.76 (d, J = 7.6 Hz, 2H), 7.92 (s, 1H, H-pyrazole), 7.96 (d, J = 8.4 Hz, 2H), 8.09-
8.12 (m, 4H); 13C NMR (400 MHz, CDCl3): δ 41.9 (C-6), 55.3 (OCH3), 55.5 (OCH3), 57.8 (C-5), 89.7 (C-2),
113.8, 114.3, 118.7, 119.2, 123.5, 124.1, 125.5, 126.3, 127.3, 127.4, 129.4, 129.5, 130.3, 139.1, 145.2, 147.1,
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150.7, 159.7, 162.7, 170.2 (C-4); after irradiation with UV light converted to red (open-form, 33%): H NMR
(400 MHz, CDCl3): δ 2.83 (s, 1H, H-6′), 3.77 (s, 1H, H-5′), 3.85 (s, 3H, OCH3), 3.92 (s, 3H, OCH3′), 6.32 (s,
1H, H-2′), 6.96-7.05 (m, 4H), 7.28 (m, 1H), 7.44-7.47 (m, 2H), 7.56 (d, J = 8.4 Hz, 2H), 7.76 (d, J = 7.6 Hz,
2H), 7.93 (s, 1H, H-pyrazole), 7.96 (d, J = 8.4 Hz 2H), 8.02 (d, J = 8.8 Hz, 2H), 8.24 (d, J = 8.4 Hz, 2H); 13C
NMR (400 MHz, CDCl3): δ 48.2 (C-6′), 55.3 (OCH3'), 55.5 (C-OCH3'), 56.8 (C-5′), 90.9 (C-2′), 113.9, 114.3,
118.7, 118.4, 122.1, 123.8, 125.9, 126.4, 126.7, 127.5, 129.3, 129.9, 130.4, 140.1, 145.2, 147.5, 150.9, 159.6,
162.7, 169.1 (C-4); UV/Vis (EtOH) λmax/nm: 290 before irradiation and 290, 425 nm after irradiation; UV/Vis
(DCM) λmax/nm: 295 before irradiation and 295, 435 nm after irradiation.
2.2.7. 6-(4-Nitrophenyl)-2-[3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl]-4-phenyl-1,3-diazabicyclo[3.1.0]hex-
3-ene (9g):
Yield: 88%; m.p. 186-188 °C; as a lemon color solid; IR (KBr, cm-1): 3057, 1597, 1511, 1449, 1342, 1246, 770,
682; (closed-form, 78%): 1H NMR (400 MHz, CDCl3): δ 2.69 (s, 1H, H-6), 3.79 (s, 1H, H-5), 6.83 (s, 1H, H-2),
7.34-7.65 (m, 8H), 7.78-7.81 (d, J = 7.6 Hz, 2H), 7.97-8.07 (m, 3H), 8.13 (d, J = 8.8 Hz, 2H), 8.26-8.35 (m,
2H), 8.46-8.50 (d, J = 8.8 Hz, 2H); 13C NMR (400 MHz, CDCl3): δ 41.9 (C-6), 58.0 (C-5), 89.6 (C-2), 119.0,
119.3, 123.7, 123.8, 127.1, 127.2, 128.2, 128.5, 129, 129.5, 131.2, 132.2, 139.2, 139.5, 144.6, 147.4, 148.1,
171.5 (C-4); after irradiation with UV light converted to green (open-form, 22%): 1H NMR (400 MHz, CDCl3):
δ 2.90 (d, J = 1.6 Hz, 1H, H-6′), 3.86 (t, J = 2.4 Hz, 1H, H-5′), 6.38 (d, J = 2.8 Hz, 1H, H-2′), 7.29 (m, 2H),
7.34-7.64 (m, 6H), 7.77-7.81 (d, J = 7.6 Hz, 2H), 7.97-8.06 (m, 5H), 8.26-8.35 (m, 4H); 13C NMR (400 MHz,
CDCl3): δ 48.2 (C-6′), 56.0 (C-5′), 90.9 (C-2′), 119.0, 123.7, 123.8, 127.1, 127.2, 128.2, 128.6, 129, 129.5,
131.2, 132.2, 139.2, 139.5, 144.6, 147.4, 148.1, 171.5 (C-4); UV/Vis (EtOH) λmax/nm: 260 before irradiation
and 265, 405 nm after irradiation; UV/Vis (DCM) λmax/nm: 260 before irradiation and 265, 415 nm after
irradiation.
2.2.8. 6-(4-Nitrophenyl)-4-phenyl-2-(1-phenyl-3-thiophen-2-yl-1H-pyrazol-4-yl)-1,3-diazabicyclo[3.1.0]hex-3-
ene (9h):
Yield: 85%; m.p. 168-169 °C; as a beige solid; IR (KBr, cm-1): 3073, 1597, 1566, 1509, 1447, 1339, 1218, 831,
1
763, 688; (closed-form, 57%): H NMR (400 MHz, CDCl3): δ 2.70 (s, 1H, H-6), 3.76 (s, 1H, H-5), 6.83 (s, 1H,
H-2), 7.20 (m, 1H), 7.29-7.62 (m, 9H), 7.74-7.79 (m, 2H), 7.89 (s, 1H), 8.02-8.05 (m, 2H), 8.02-8.05 (s, 1H),
8.11-8.15 (m, 2H); 13C NMR (400 MHz, CDCl3): δ 42.0 (C-6), 57.9 (C-5), 89.6 (C-2), 117.8, 118.8, 121.7,
123.6, 125.4, 126.5, 126.7, 127.3, 127.5, 127.7, 128.6, 128.9, 129.4, 131.4, 132.8, 135.1, 139.5, 145.5, 147.5,
171.3 (C-4); after irradiation with UV light converted to blue (open-form, 43%): 1H NMR (400 MHz, CDCl3): δ
2.91 (d, J = 1.6 Hz, 1H, H-6'), 3.81 (t, J = 2.4 Hz, 1H, H-5'), 6.45 (d, J = 2.4 Hz, 1H, H-2'), 7.10 (m, 1H), 7.29-
7.62 (m, 9H), 7.74-7.79 (m, 3H), 7.94 (s, 1H), 8.11-8.15 (m, 2H), 8.25 (d, J = 8.8 Hz, 2H); 13C NMR (400 MHz,