Organic Electroluminescence
4706±4714
1
Pentamer 4: H NMR (300 MHz, CDCl
7
3
, 258C, TMS): d 7.72 (m, 2H),
132.21, 132.01, 131.86, 131.78, 129.05, 128.67, 128.65, 126.18, 125.94, 124.07,
124.00. 123.94, 123.88, 123.48, 123.47, 123.36, 123.28, 107.00*, 93.78, 93.39*,
93.19, 91.45, 91.30, 90.83, 90.45, 90.17, 89.39, 19.09, 11.71; MS (APCI): m/z:
1
3
.45 ± 7.52 (m, 16H), 7.32 ± 7.37 (m, 2H), 1.41 (s, 42H); C NMR (75 MHz,
CDCl
3
, 258C): d 135.04, 132.42, 132.03, 131.87, 131.82, 128.97, 123.97,
1
1
[
23.87, 123.82, 123.43, 123.20, 106.98, 93.36, 90.84, 90.64, 90.19, 90.10, 19.08,
1.70; MS (MALDI-Tof, a-cyano-4-hydroxycinnamic acid): m/z: 1678.1
880.3 [MK] , 838.2 [M] ; elemental analysis calcd (%) for C60
H62Si
2
(839.4): C 85.85, H 7.46; found: C 85.42, H 7.75.
2M] , 839.4 [M] ; elemental analysis calcd (%) for C60
5.85, H 7.46; found: C 85.61, H 7.62.
H
62Si
2
(839.4): C
1
Pentamer 14: H NMR (300 MHz, CDCl
7
3
, 258C, TMS): d 7.69 (m, 1H),
8
.71 (t, J 1.6 Hz, 1H), 7.6 ± 7.4 (m, 14H), 7.4 ± 7.3 (m, 4H), 1.14 (s, 21H),
1
13
Pentamer 5: H NMR (300 MHz, CDCl
3
, 258C, TMS): d 7.72 (m, 1H),
1.12 (s, 21H); C NMR (75 MHz, CDCl , 258C): d 135.12, 135.05, 132.45,
3
1
3
7
.40 ± 7.53 (m, 18H), 7.35 (m, 1H), 1.14 (s, 42H); C NMR (75 MHz,
132.41, 132.29, 131.93, 131.85, 131.83, 129.04, 128.99, 128.67, 128.65, 126.12,
125.94, 124.05, 123.99, 123.94, 123.86*, 123.79, 123.47, 123.25, 107.01*, 93.79,
93.36, 93.32, 93.15, 90.70, 90.43, 90.16, 89.58, 89.54, 89.33, 19.29, 11.71; MS
CDCl
3
, 258C): d 135.04, 132.42, 132.03, 132.00, 131.86, 131.82, 131.80,
1
1
1
28.98, 123.98*, 123.88, 123.82, 123.49, 123.44*, 123.40, 123.21, 123.20,
06.98*, 93.41, 93.37, 91.54, 91.45*, 91.25, 90.88, 90.63, 90.19, 90.11, 19.08,
1.70; MS (MALDI-Tof, a-cyano-4-hydroxycinnamic acid): m/z: 1677.6
2M] , 839.3 [M] ; elemental analysis calcd (%) for C60
5.85, H 7.46; found: C 86.03, H 7.07.
(APCI): m/z: 880.3 [MK]
C H Si (CH OH) (849.34): C 85.27, H 7.52; found: C 85.28, H 7.52.
, 839.0 [M] ; elemental analysis calcd (%) for
60
62
2
3
0.31
[
H
62Si
2
(839.4): C
1
Pentamer 15: H NMR (300 MHz, CDCl
3
, 258C, TMS): d 7.83 (m, 1H),
8
7
1
1
.30 ± 7.60 (m, 19H), 1.13 (s, 42H); 13C NMR (75 MHz, CDCl
35.18, 132.44, 132.29, 131.81, 129.10, 128.65, 126.10, 125.90, 124.10, 123.93,
23.43, 107.07, 93.78, 93.21, 93.15, 90.39, 89.37, 19.09, 11.90; MS (MALDI-
3
, 258C): d
1
Pentamer 6: H NMR (300 MHz, CDCl
3
, 258C, TMS): d 7.72 (m, 2H),
1
3
7
.60 ± 7.74 (m, 16H), 7.30 ± 7.36 (m, 2H), 1.26 (s, 42H); C NMR (75 MHz,
CDCl
3
, 258C): d 135.07, 132.42, 132.03, 131.99, 131.94, 131.90, 131.83,
Tof, a-cyano-4-hydroxycinnamic acid): m/z: 1678.6 [2M] , 795.1 [M �
1
1
8
31.81, 128.97, 123.97*, 123.88, 123.84*, 123.81, 123.48, 123.39, 123.24,
iPr] ; MS (APCI): m/z: 880.0 [MK] , 839.2 [M] .
23.22, 107.00*, 93.40, 93.36, 91.50, 91.26, 90.86, 90.66, 90.20, 90.15, 89.57,
9.53, 19.08, 11.71; MS (MALDI-Tof, a-cyano-4-hydroxycinnamic acid):
1
Pentamer 16: H NMR (300 MHz, CDCl
3
, 258C, TMS): d 7.30 ± 7.63 (m,
2
1
1
1
9
0H), 1.14 (s, 21H), 1.13 (s, 21H); 13C NMR (75 MHz, CDCl
3
, 258C): d
m/z: 1677.6 [2M] ; MS (APCI): m/z: 880.0 [MK] , 836.6 [M] ; elemental
32.44, 132.40, 132.27, 132.25, 132.06, 131.87, 131.82, 131.77, 128.69, 128.65,
28.60, 126.26, 126.23, 125.99, 125.95, 123.91, 123.76, 123.64, 123.45, 123.29,
23.24, 107.12, 107.01, 93.89, 93.86, 93.35, 93.13, 92.70, 92.68, 91.38, 91.35,
0.65, 90.41, 19.08, 11.71; MS (MALDI-Tof, a-cyano-4-hydroxycinnamic
analysis calcd (%) for C60
H
62Si
2
(CH
3
OH)0.5 (871.45): C 84.93, H 7.55;
found: C 84.96, H 7.83.
1
Pentamer 7: H NMR (300 MHz, CDCl
3
, 258C, TMS): d 7.72 (m, 3H),
1
3
7
.40 ± 7.54 (m, 14H), 7.30 ± 7.40 (m, 3H), 1.14 (s, 42H); C NMR (75 MHz,
acid): m/z: 1678.4 [2M] , 839.4 [M] ; MS (APCI): m/z: 880.0 [MK] ,
CDCl
3
, 258C): d 135.07, 132.42, 131.93, 131.91, 131.88, 131.83, 128.97,
8
39.2 [M] .
1
1
[
23.96, 123.86, 123.828, 123.21, 106.99, 93.35, 90.65, 90.18, 89.54*, 19.08,
1.73; MS (MALDI-Tof, a-cyano-4-hydroxycinnamic acid): m/z: 1678.9
1
Pentamer 17: H NMR (300 MHz, CDCl
7.20 ± 7.65 (m, 19H), 1.14 (s, 21H), 1.12 (s, 21H); C NMR (75 MHz,
CDCl
3
, 258C, TMS): d 7.70 (m, 1H),
13
2M] ; MS (APCI): m/z: 880.4 [MK] , 839.1 [M] ; elemental analysis
3
, 258C): d 135.40, 132.52, 132.40, 132.38, 132.25, 132.22, 131.86,
calcd (%) for C60
H
62Si
2
(839.4): C 85.85, H 7.46; found: C 85.48, H 7.70.
, 258C, TMS): d 7.75 (m, 2H),
, 258C): d
35.17, 132.35, 132.15, 131.86, 131.82, 129.01, 128.66, 126.16, 124.03, 123.92,
1
1
1
1
31.83, 131.81, 131.65, 128.79, 128.68, 128.63, 128.60, 126.36, 126.23, 125.97,
1
Pentamer 8: H NMR (300 MHz, CDCl
3
25.94, 107.11, 107.00, 93.88, 93.30, 93.13, 92.69, 90.77, 90.45, 89.96, 89.35,
9.07, 11.71; MS (MALDI-Tof, a-cyano-4-hydroxycinnamic acid): m/z:
1
3
7
.30 ± 7.59 (m, 18H), 1.14 (s, 42H); C NMR (75 MHz, CDCl
3
1
1
677.4 [2M] ; MS (APCI): m/z: 879.9 [MK] , 838.9 [M] .
23.88, 123.21, 107.01, 93.27, 93.25, 90.64, 90.17, 89.34, 19.08, 11.71; MS
MALDI-Tof, a-cyano-4-hydroxycinnamic acid): m/z: 1677.6 [2M] 839.3
M] ; elemental analysis calcd (%) for C60
found: C 85.51, H 7.23.
1
Pentamer 18: H NMR (CDCl , 300 MHz): d 7.10 ± 7.70 (m, 20H), 1.13 (s,
(
[
3
42H); 13C NMR (CDCl , 75 MHz): d 132.62, 132.55, 132.22, 132.07,
H
62Si
2
(839.4): C 85.85, H 7.46;
3
1
9
31.81, 128.64, 128.47, 128.41, 126.19, 126.10, 125.88, 123.67, 123.50, 107.17,
3.72, 93.00, 92.82, 92.70, 90.47, 19.08, 11.70; MS (MALDI-Tof, a-cyano-4-
hydroxycinnamic acid): m/z: 1677.4 [2M] , 839.1 [M] ; MS (APCI): m/z:
1
Pentamer 9: H NMR (300 MHz, CDCl
3
, 258C, TMS): d 7.77 (m, 1H),
1
3
7
.30 ± 7.60 (m, 19H), 1.14 (s, 21H), 1.12 (s, 21H); C NMR (75 MHz,
8
38.9 [M] .
CDCl
3
, 258C): d 135.25, 132.43, 132.19, 132.14, 132.04, 131.86, 131.76,
1
1
8
31.69, 129.02, 128.68, 126.20, 126.05, 124.03, 123.96*, 123.90, 123.63, 123.51,
Photophysical experiments: Absorption spectra were measured on a
Shimadzu 2401PC spectrophotometer. Photoluminescence spectra of
materials in solution were measured with a Perkin ± Elmer LS50B
23.18*, 107.01, 106.96, 93.79, 93.31*, 93.28, 91.55, 91.25, 90.66, 90.60, 90.19,
9.38, 19.07, 18.86, 11.71, 11.68; MS (MALDI-Tof, a-cyano-4-hydroxycin-
namic acid): m/z: 1678.6 [2M] , 839.3 [M] ; elemental analysis calcd (%)
spectrophotometer. The photoluminescence quantum yields in dichloro-
methane were measured by comparison with anthracene in ethanol
for C60H
62Si
2
(839.4): C 85.85, H 7.46; found: C 86.11, H 7.45.
[
17]
1
(27%). The solid-state photoluminescence spectra were measured by
using an Edinburgh Instruments FS900CDT spectrofluorimeter.
Pentamer 10: H NMR (300 MHz, CDCl
8H), 7.30 ± 7.40 (m, 2H). 1.14 (s, 42H); C NMR (75 MHz, CDCl , 258C):
3
3
, 258C, TMS): d 7.40 ± 7.60 (m,
13
1
d 132.46, 132.42, 132.23, 132.05, 132.00, 131.80, 128.69, 128.66, 126.07,
Thin films (ca. 50 nm) of the pentamers for photoluminescence were
prepared by spin-coating onto fused silica from toluene (15 mgmL ) at
4 krpm for 40 s, and their photoluminescence characteristics investigated in
air.
�
1
1
9
26.00, 124.00, 123.97, 123.68, 123.47, 123.44*, 123.42, 123.22, 106.99*, 93.81,
3.75, 93.41*, 91.53, 91.49*, 91.26, 90.67, 90.41, 19.08, 11.71; MS (APCI):
m/z: 880.2 [MK] , 838.0 [M] ; elemental analysis calcd (%) for C60
H62Si
2
(
839.4): C 85.85, H 7.46; found: C 85.76, H 7.17.
� 1
Electroluminescence: ITO on glass with a sheet resistivity of 20 Wsquare
1
Pentamer 11: H NMR (300 MHz, CDCl
7
3
, 258C, TMS): d 7.72 (m, 1H),
was obtained from Merck; it was cleaned by sonication in Decon, followed
by 2% sodium hydroxide solution, washed with deionised water and then
dried from iso-propanol. The ITO on glass was then patterned, by etching,
into 2 mm width strips, and then cleaned again, before depositing any
organic layers. The metal cathodes (2 mm width strips) were evaporated
normal to the ITO strips, thus defining 2 mm  2mm pixels. The luminance/
current/voltage characteristics were measured by using a Topcon BM-7
luminance meter and a current/voltage measuring unit (Kiethley SM4236)
1
3
.40 ± 7.60 (m, 16H), 7.30 ± 7.40 (m, 3H), 1.14 (s, 42H); C NMR (75 MHz,
CDCl
3
, 258C): d 135.06, 132.46, 132.41, 132.23, 132.07, 131.97, 131.87,
1
1
9
31.82, 131.79, 128.97, 128.68, 128.65, 126.07, 126.01, 124.00, 123.96, 123.87,
23.84, 123.67, 123.44*, 123.21, 106.99*, 93.80, 93.74, 93.40, 93.35, 90.87,
0.65, 90.62, 90.41, 90.18, 90.15, 19.08, 11.71; MS (APCI): m/z: 880.0
[
(
MK] , 838.0 [M] ; elemental analysis calcd (%) for C60
2 6 14 0.76
H62Si (C H )
904.91): C 85.65, H 8.10; found: C 85.37, H 8.11.
1
under N . Electroluminescence spectra were measured by using an
Pentamer 12: H NMR (300 MHz, CDCl
1
3
, 258C, TMS): d 7.40 ± 7.60 (m,
2
1
3
Edinburgh Instruments FS900CDT spectrofluorimeter.
6H), 7.30 ± 7.40 (m, 4H), 1.13 (s, 42H); C NMR (75 MHz, CDCl
d 132.46, 132.25, 132.02, 131.78, 128.67, 128.64, 126.07, 126.01, 124.01,
23.68, 123.42, 106.97, 93.83, 93.77, 93.38, 90.64, 90.38, 19.08, 11.70; MS
3
, 258C):
� 1
ITO/pentamer 3 (150 nm)/Al:Li: Pentamer 3 (45 mg mL ) in toluene was
1
(
deposited (150 nm) onto ITO-glass by spin-coating under nitrogen (2 krpm
for 40 s); the substrate was then placed in the evaporation chamber without
exposure to air and pumped overnight. The aluminium lithium cathode was
APCI): m/z: 881.0 [MK] , 839.0 [M] ; elemental analysis calcd (%) for
C
60
H
62Si
2
(CH
3
OH)0.52 (856.07): C 84.90, H 7.56; found: C 84.90, H 7.48.
1
� 7
Pentamer 13: H NMR (300 MHz, CDCl
7
3
, 258C, TMS): d 7.78 (m, 1H),
evaporated at 10 mbar. ꢁ5% lithium was incorporated into the
.40 ± 7.60 (m, 16H), 7.30 ± 7.40 (m, 3H), 1.14 (s, 21H), 1.13 (s, 21H);
C NMR (75 MHz, CDCl
aluminium cathode by coevaporating aluminium and lithium; the lithium
was evaporated from a getter supplied by SAES Getters.
1
3
3
, 258C): d 135.20, 132.46, 132.42, 132.28,
ꢀ WILEY-VCH Verlag GmbH, D-69451 Weinheim, 2001
Chem. Eur. J. 2001, 7, No. 21
0947-6539/01/0721-4713 $ 17.50+.50/0
4713