ACCEPTED MANUSCRIPT
A
mixture
,6'-bis((3',4',5'-tris(hexyloxy)-[1,1'-biphenyl]-4-yl)oxy)-2,2'-bi
pyridine (L ) (0.2g, 0.18 mmol), K PtCl (0.09 g, 0.22 mmol)
of
8.2 Hz), 6.81 (4H s), 3.86 (12H dd, J = 29.3, 22.8 Hz), 1.79 –
13
6
1.58 (12H m), 1.26 (156H s), 0.88 (18H t, J = 6.7 Hz). C NMR
(100 MHz, CDCl ) δ (ppm): 155.7, 155.7, 153.4, 153.3, 153.1,
6
2
4
3
and glacial acetic acid (10 ml) was sealed in a Schlenk tube
and refluxed under nitrogen for 48 hours. After extracted,
dried and filtrated, the filtrate was reduced pressure
evaporated to remove solvent. The pure viscous orange liquid
152.4, 140.0, 138.3, 137.2, 136.00, 126.1, 122.2, 122.1, 122.1,
115.6, 105.0, 77.3, 77.2, 77.0, 76.7, 73.4, 68.9, 32.0, 30.4,
30.0, 30.0, 29.8, 29.8, 29.7, 29.6, 29.5, 29.4, 26.2, 22.7, 14.2.
+
HRMS (ESI+) cacld for [M + Na] : 2149.5946; found: m/z =
(
0.17 g, 73 %) was got from column chromatography (PE:EA =
2149.5952. Elem. Anal. Cacld for C130H214N O Pt (2126.6048):
2
8
1
1
.5:1). H NMR (400 MHz, CDCl ) δ = 8.15 (2H s), 7.97 (2H q,
C 73.37, H 10.14, N 1.32; found C 73.30, H 10.02, N 1.27.
3
H
J = 8.2 Hz), 7.66 (2H d, J = 7.6 Hz), 7.39 (4H d, J = 8.3 Hz), 7.33
–
1
7.27 (2H m), 6.84 (4H d, J = 9.8 Hz), 4.10 – 3.71 (12H m),
.92 – 1.63 (12H m), 1.42 – 1.18 (36H m), 0.89 (18H t, J = 6.7
5 Conclusion
1
3
Hz). C NMR (100 MHz, CDCl ) δ (ppm): 155.6, 153.3, 153.2,
A new kind of tetradentate platinum(II) complexes were
synthesized. The columnar metallomesogen based on the
tetradentate ligand was obtained by carefully balancing the
number and length of alkoxyl chains around platinum(II)
complex. The complex shows ambipolar carrier transport
property in columnar mesogenic phase. Our results provide a
possible access to achieving ambipolar carrier transport in
the single material.
3
1
1
3
1
53.1, 152.4, 140.0, 138.3, 137.2, 136.0, 136.5, 126.1, 122.1,
17.0, 115.6, 105.6, 105.0, 77.4, 77.0, 76.7, 73.4, 69.1, 31.7,
+
0.3, 29.7, 25.8, 22.7, 14.1. HRMS (ESI+) cacld for [M + Na] :
308.6556; found: m/z = 1308.6556. Elem. Anal. Cacld for
C H N O Pt (1285.6658): C 65.35, H 7.36, N 2.18; found C
0 94 2 8
7
6
5.27, H 7.21, N 2.12.
4
.2.12.
Pt-6,6'-bis((3',4',5'-tris(dodecyloxy)-[1,1'-biphenyl]-4-yl)oxy)-2,
'-bipyridine (Pt ).
Acknowledgements
2
We are grateful to National Natural Science Foundation of
China (21172161) for financial support and Prof. Qiang Peng
from Sichuan University for assistance of device fabrication.
12
The synthetic method of the substance is the same as Pt6.
1
The yield of orange solid was 71 %. H NMR (400 MHz, CDCl )
3
δH = 8.14 (2H s), 7.88 (2H t, J = 7.9 Hz), 7.53 (2H d, J = 7.6 Hz),
7
4
1
.40 (2H d, J = 8.4 Hz), 7.32 (2H d, J = 8.4 Hz), 7.27 (2H d, J =
.4 Hz), 6.83 (4H s), 3.87 (12H dd, J = 29.4, 22.9 Hz), 1.79 –
.56 (12H m), 1.31 (108H d, J = 35.4 Hz), 0.98 – 0.75 (18H m).
References
[1]
Lamansky S, Djurovich P, Murphy D, Abdel-Razzaq F,
Lee HE, Adachi C, et al. Highly phosphorescent
bis-cyclometalated iridium complexes: Synthesis,
photophysical characterization, and use in organic
light emitting diodes. J Am Chem Soc
13
C NMR (100 MHz, CDCl ) δ (ppm): 156.0, 153.6, 153.3,
3
1
1
3
53.1, 152.4, 140.0, 138.3, 137.2, 136.0, 135.7, 126.0, 122.3,
16.7, 115.9, 115.6, 105.0, 77.3, 77.0, 76.7, 73.4, 68.9, 37.1,
1.9, 30.4, 29.7, 29.5, 27.1, 26.2, 22.7, 19.7, 14.1. HRMS (ESI+)
2001;123:4304–12.
+
cacld for [M + Na] : 1813.2190; found: m/z = 1813.2190.
[2]
[3]
[4]
Brooks J, Babayan Y, Lamansky S, Djurovich PI, Tsyba
I, Bau R, et al. Synthesis and Characterization of
Phosphorescent Cyclometalated Platinum
Elem. Anal. Cacld for C106H166N O Pt (1790.2292): C 71.06, H
2
8
9
.34, N 1.56; found C 71.01, H 9.22, N 1.51.
Complexes. Inorg Chem 2002;41:3055–66.
Leopold H, Tronnier A, Wagenblast G, Münster I,
Strassner T. Photoluminescence of a New Material:
Cyclometalated C^C∗ Thiazole-2-ylidene Platinum(II)
Complexes. Organometallics 2016;35:959–71.
Choy WCH, Chan WK, Yuan Y. Recent advances in
transition metal complexes and light-management
engineering in organic optoelectronic devices. Adv
4
.2.13.
Pt-6,6'-bis((3',4',5'-tris(hexadecyloxy)-[1,1'-biphenyl]-4-yl)oxy)
2,2'-bipyridine (Pt ).
-
16
The synthetic method of the substance is the same as Pt6.
1
The yield of orange solid was 74 %. H NMR (400 MHz, CDCl )
3
δH = 8.16 (2H s), 8.04 (2H t, J = 7.9 Hz), 7.73 (2H d, J = 7.7 Hz),
7
.43 (2H d, J = 8.5 Hz), 7.39 (2H d, J = 8.4 Hz), 7.29 (2H d, J =