Amor phous Solid of Low Molecular Weight Diamine
J. Chin. Chem. Soc., Vol. 48, No. 6A, 2001 1063
solvedintetrahydrofuranandtheproductwasprecipitatedby
theadditionofethanol.Theisolatedyieldsaswellasspectro-
scopic data for all new com pounds in Ta ble 1 are re ported be-
low. For the known com pounds, iso lated yields are col lected
in Ta ble 1, and all spec tro scopic data are con sis tent with
thosereportedinliterature.
4.34; found: C, 88.94; H, 6.34; N, 4.71. HRMS cal cu lated
644.3191; found 644.3186.
Data for N,N -bis(2-naphthyl)-N,N -bis(3-ethylphenyl)-
1,1 -biphenyl-4,4 -diamine (4h)
Light yellow solid, isolated yield 81%. 1H-NMR
(CDCl3, 300 MHz) 1.21 (t,J = 7.63 Hz, 3H); 2.88 (q,J = 7.57
Hz, 2H); 6.93 (d, J = 7.5 Hz, 1H); 6.99 (d, J = 7.89 Hz, 1H);
7.05 (s, 1H); 7.20 (m, 3H); 7.38 (m, 3H); 7.49 (m, 2H); 7.61
(d, J = 7.82 Hz, 1H); 7.75 (m, 2H). 13C-NMR (100 MHz,
CDCl3) 15.54, 28.77, 120.19, 121.99, 122.76, 124.12,
124.23, 124.40, 124.47, 126.22, 126.89, 127,26, 127.52,
128.80, 129.16, 129.98, 134.42, 134.72, 145.43, 145.59,
146.78, 147.57. UV/VIS max (log ) 351 (4.55) 322 (4.534)
Data for N,N -bis(2-naphthyl)-N,N -bis(3-methylphenyl)-
1,1 -biphenyl-4,4 -diamine (4b)
Light yel low solid prod uct, iso lated yield 85%. 1H-
NMR (600 MHz, CDCl3): 2.27 (s, 3H), 6.88 (d, J = 8.0 Hz,
1H), 6.98 (m, 2H), 7.17 (m, 3H), 7.35 (m, 3H), 7.45 (m, 3H),
7.59 (d, J = 7.6 Hz, 1H), 7.75 (d, J = 7.6 Hz, 1H). 13C-NMR
(150 MHz): 21.41 (CH3), 120.30, 121.84, 124.07, 124.26,
124.44, 124.49, 125.29, 126.24, 126.93, 127.30, 127.55,
128.84, 129.13, 130.04, 134.46, 134.80, 139.21, 145.47,
275 (4.45). Emis sion Spec trum
(CHCl3): 444.5 nm. El e-
max
mentalanalysiscalculatedforC48H40N2: C, 89.40; H, 6.25;
N, 4.34; found: C, 89.2; H, 6.19; N, 4.61. HRMS cal cu lated
644.3191; found 644.3184.
146.81, 147.62. UV/VIS (CHCl3)
(log ): 356 (4.56),
max
329(4.57), 285(4.47). EmissionSpectrum max (CHCl3): 452
nm.ElementalanalysiscalculatedforC46H36N2: C, 89.58; H,
5.88; N, 4.54; found: C, 89.35; H, 5.96; N, 4.86; HRMS cal-
cu lated. 616.2878; found 616.2875.
ACKNOWLEDGMENT
Data for N,N -diphenyl-N,N -bis(3-ethylphenyl)-1,1 -
biphenyl-4,4 -diamine (4f)
We thank the Na tional Sci ence Coun cil of Tai wan for
fi nan cial sup port (NSC 88-2113-M-007-038 and 89-2113-
M-007-027)andtheInstituteofIndustrialResearch.
Light yel low solid, iso lated yield 76%. 1H-NMR (300
MHz, CDCl3) 1.18 (t, J = 7.56 Hz, 3H); 2.56 (q, 7.56, 2H);
6.88 (d, J = 7.46 Hz, 1H); 6.93 (dd,J1 = 8.08 Hz,J2 = 1.97 Hz,
1H); 7.00 (m, 2H); 7.19 (m, 7H); 7.45 (d, J = 8.44 Hz, 2H).
13C-NMR (75 MHz, CDCl3) 15.39, 28.82, 121.96, 122.66,
124.09, 124.27, 127.24, 129.18, 134.75, 145.59, 146.99,
Received January 15, 2001.
Key Words
147.82, 148.00. UV/VIS (CHCl3)
329 (3.53). Emis sion Spec trum
(log ): 352 (3.47),
Amorphous materials; Triarylamine; Lumines-
cence; Phase transitions.
max
(CHCl3) 438 nm. El e-
max
mentalanalysiscalculatedforC40H36N2: C, 88.19; H, 6.66;
N, 5.14; found: C, 87.82; H, 6.79; N, 5.42. HRMS cal cu lated
544.2878; found 544.2872.
REFERENCES
Data for N,N -bis(1-naphthyl)-N,N -bis-(3-ethylphenyl)-
1,1 -biphenyl-4,4 -diamine (4g)
1. (a) Van slyke, S. A.; Tang, C. W. US pat ent 4,539,507,
1985. (b) Tang, C. W.; Van slyke, S. A. Appl. Phys. Lett.
1987, 51, 913. (c) Adachi, C.; Tsutui, T.; Saito, S. Appl.
Phys. Lett. 1990, 57, 531. (d) Shirota, Y.; Kuwabara, Y.;
Inada, H.; Wakimoto, T.; Nakada, H.; Yonemoto, Y.;
Kawai, S.; Imai, K. Appl. Phys. Lett. 1994, 65, 807. (e)
Van Slyke, S. A.; Chen, C. H.; Tang, C. W. Appl. Phys.
Lett. 1996, 69, 2160. (f) Tutsui, T. MRSBulletin1997, 39.
(g) Chen, C. H.; Shi, J.; Tang, C. W. Macromol. Sym.
1998, 125, 1.
Light yel low solid, iso lated yield 73%. 1H-NMR (300
MHz, CDCl3) 1.15 (t, J = 7.58 Hz, 3H); 2.52 (d, J = 7.54 Hz,
2H); 6.81 (d,J = 7.49 Hz, 1H); 6.85 (d,J = 7.99 Hz, 1H); 7.02
(d, J = 8.54 Hz, 2H); 7.11 (dd,J1 = 7.84 Hz, J2 = 7.73 Hz, 1H);
7.42 (m, 6H); 7.76 (d,J = 8.11, 1H); 7.88 (d,J = 8.07 Hz, 1H);
7.96 (d, J = 8.33 Hz, 2H). 13C-NMR (75 MHz, CDCl3) 15.35,
28.85, 119.80, 121.58, 121.93, 124.48, 126.06, 126.30,
127.03, 128.35, 129.00, 131.48, 135.42, 143.82, 145.39,
147.60, 148.55. UV/VIS (CHCl3) max (log ) 345 (3.55), 272
(3.36). EmissionSpectrum max (CHCl3):474.5nm. Elemen-
tal anal y sis cal cu lated for C48H40N2: C, 89.40; H, 6.25; N,
2. (a) Kido, J.; Kimura, M.; Nagai, K. Science 1995, 267,
1132. (b) Kido, J. BulletinofElectrochemistry. 1994, 10,
1.