Synthesis and Photoluminescent Properties of New Ceramidine Derivatives 71
8.68 (d, J = 7.3 Hz, 1H), 8.76 (d, J = 8.9 Hz, 1H). 13
C
7.43–7.53 (m, 11H), 7.59–7.64 (m, 3H), 8.17 (d, J
= 6.5 Hz, 1H), 8.34 (d, J = 6.0 Hz, 1H), 8.42 (d, J =
5.6 Hz, 1H), 8.53–8.58 (m, 2H). 13C NMR (100 MHz,
CDCl3): δ (ppm) 50.4, 121.3, 123.1, 125.8, 127.0,
127.2, 127.7, 128.6, 128.8, 129.6, 129.8, 130.0, 130.2,
130.6, 131.6, 132.6, 133.2, 133.6, 135.5, 139.3, 140.8,
142.7, 150.0, 151.1, 183.0.
NMR (75 MHz, CDCl3): δ (ppm) 51.2, 121.3, 123.2,
125.3, 125.8, 127.1, 127.2, 127.6, 128.6, 128.7, 128.8,
129.6, 129.8, 130.1, 130.6, 131.6, 132.5, 133.3, 133.6,
135.6, 141.2, 141.3, 144.0, 145.3, 150.0, 151.1, 183.1.
Dinaphthalen-2-ylmethanol 5d
Compound 5d was synthesized as with compound
6b. Yield: 2.3 g (79%). mp: 113◦C. IR (KBr): 3325,
1599, 1507, 1362, 1272, 1162, 1119, 1028, 859, 824,
789, 756 cm−1. 1H NMR (300 MHz, CDCl3): δ (ppm)
2.61 (s, 1H), 6.16 (s, 1H), 7.48–7.53 (m, 6H), 7.81–
7.86 (m, 6H), 7.96 (s, 2H). 13C NMR (75 MHz, CDCl3):
δ (ppm) 76.5, 124.9, 125.3, 126.1, 126.3, 127.7, 128.1,
128.4, 133.0, 133.3, 141.0.
Dibiphenyl-3-ylmethanol 1c
Compound 1c was synthesized as with compound
1b. Pale yellow oil. Yield: 11.3 g (78%). IR (KBr):
3408, 1598, 1479, 1453, 1423, 1168, 1032, 898, 758,
699 cm−1. 1H NMR (300 MHz, CDCl3): δ (ppm) 2.58
(s, 1H), 5.99 (s, 1H), 7.39–7.43 (m, 2H), 7.45–7.51
(m, 8H), 7.55–7.58 (m, 2H), 7.63–7.66 (m, 4H), 7.73
(s, 2H). 13C NMR (75 MHz, CDCl3): δ (ppm) 76.4,
125.4, 125.6, 126.5, 127.3, 127.4, 128.8, 129.1, 141.1,
141.6, 141.3.
2,2ꢁ-(Bromomethylene)dinaphthalene 1d
Compound 1d was synthesized as with compound
1b. Yield: 2.6 g (98%). mp: 168◦C. IR (KBr): 3429,
(Dibiphenyl-3-ylmethyl)triphenylphosphonium
Bromide 6c
1
1507, 865, 778, 754, 688 cm−1. H NMR (300 MHz,
CDCl3): δ (ppm) 6.68 (s, 1H), 7.42 (s, 1H), 7.54 (s,
3H), 7.69 (d, J = 8.2 Hz, 2H), 7.87–7.95 (m, 8H). 13
C
To a solution of compound 1c (11 g, 33 mmol) in dry
benzene (100 mL) was added acetyl bromide (40.2 g,
330 mmol) and the resulting mixture was refluxed
for 4 h, then cooled to room temperature. The sol-
vent and excess acetyl bromide were removed by us-
ing a rotary evaporator. The resulting crude mixture
and triphenylphosphine (11.3 g, 43 mmol) were dis-
solved in toluene (30 mL), and the reaction mixture
was refluxed with vigorous stirring for 12 h, dur-
ing which time a white solid was precipitated from
the solution. The reaction mixture was placed in the
freezer at −10◦C for 4 h and then filtered to collect
the solid, which was washed with hot ethyl acetate to
give a pure product 6c as a white solid. Yield: 11.4 g
(52%). mp: 238◦C. IR (KBr): 3430, 3054, 2801, 1597,
1482, 1436, 1105, 755, 697 cm−1. 1H NMR (300 MHz,
CDCl3): δ (ppm) 7.30–7.32 (m, 12H), 7.50–7.85 (m,
22H). 13C NMR (75 MHz, CDCl3): δ (ppm) 45.3, 45.8,
118.2, 119.3, 126.8, 127.2, 127.6, 128.8, 129.4, 129.5,
129.6, 129.9, 130.1, 130.2, 130.3, 133.6, 133.7, 134.8,
135.2, 135.3, 139.7, 141.4.
NMR (75 MHz, CDCl3): δ (ppm) 56.3, 126.58, 126.7,
127.4, 127.7, 128.3, 128.4, 128.6, 133.0, 133.0, 138.2.
(Dinaphthalen - 2 - ylmethyl)triphenylphosphoni-
um Bromide 6d
Compound 6d was synthesized as with compound
6a. Yield: 2.8 g (78%). mp: 240◦C. IR (KBr): 3433,
3055, 2754, 1504, 1436, 1104, 737, 690 cm−1. 1H NMR
(300 MHz, CDCl3): δ (ppm) 7.27–7.34 (m, 4H), 7.47
(s, 8H), 7.55–7.62 (m, 7H), 7.73–7.80 (m, 8H), 7.88
(s, 2H). 13C NMR (75 MHz, CDCl3): δ (ppm) 126.5,
126.9, 127.5, 128.2, 128.3, 128.3, 128.8, 129.9, 130.1,
130.6, 130.7, 130.8, 130.9, 132.7, 132.8, 135.0, 135.1,
135.2.
9-(Dinaphthalen-2-ylmethylene)-9H-naphtho [3,
2,1-kl]acridine 8d
Compound 8d was synthesized as with compound
8a. Yield: 123 mg (43%). mp: 190◦C. IR (KBr): 3436,
1652, 1522, 1306, 769, 703 cm−1. Elemental analyses
(C41H25N) calcd: C, 92.63; H, 4.74; N, 2.63. Found: C,
9-(Dibiphenyl-3-ylmethylene)-9H-naphtho[3,2,
1-kl]acridine 8c
1
92.21; H, 4.91; N, 2.22. H NMR (300 MHz, CDCl3):
Compound 8c was synthesized as with compound
8a. Yield: 1.2 g (11%). mp: 130◦C. IR (KBr): 3435,
1655, 1597, 1522, 1306, 760, 700 cm−1. Elemental
analyses (C45H29N) calcd: C, 92.59; H, 5.01; N, 2.40.
Found: C, 92.00; H, 5.45; N, 2.99. 1H NMR (300 MHz,
CDCl3): δ (ppm) 7.31–7.70 (m, 21H), 7.76–7.81 (m,
3H), 8.32 (d, J = 8.6 Hz, 1H), 8.55 (d, J = 9.1 Hz, 2H),
δ (ppm) 7.44–7.45 (m, 4H), 7.56–7.61 (m, 3H), 7.66–
7.85 (m, 13H), 8.28 (d, J = 8.3 Hz, 1H), 8.52 (d, J =
7.5 Hz, 1H), 8.57 (d, J = 7.5 Hz, 1H), 8.67 (d, J =
7.2 Hz, 1H), 8.73 (d, J = 8.6 Hz, 1H). 13C NMR
(75 MHz, CDCl3): δ (ppm) 51.3, 121.3, 123.1, 125.7,
125.8, 126.0, 127.2, 127.6, 127.6, 127.9, 128.1, 128.2,
128.5, 128.7, 129.6, 129.8, 130.4, 130.6, 131.6, 132.3,
Heteroatom Chemistry DOI 10.1002/hc