Post on 04-Jan-2016
description
Development of Polymer Systems with High Electron Mobility for
Photovoltaic Applications
Development of Polymer Systems with High Electron Mobility for
Photovoltaic Applications
Jie Hu, Dong Zhang, Shi Jin, Stephen Z.D. Cheng and Frank W.
Harris
The Maurice Morton Instituteof Polymer Science
The University of AkronAkron, OH 44325-3909
To develop materials with high
electron mobility for photovoltaic
applications
ObjectiveObjective
Utilization of nitrogen-containing heterocyclic
structures
N
R
R
Ar' Ar* *
n
X
Poly(pyridinium salts) Poly(quinoxalines)
N
N
*
*
R
ApproachApproach
Specific objective of this work is to develop discotic/planar liquid crystalline compounds that display high electron mobilities.
Discotic liquid crystalline compounds have been prepared that exhibit high hole mobilities.
Adam, D.; Schumacher, P.; Simmerer, J.; Haussling, L.; Siemersmeyer, K.; Etzbach, K.H.; Ringsdorf, H.; Haarer, D. Nature 1994, 371, 141.
Discotic Liquid Cyrstalline Compounds
Discotic Liquid Cyrstalline Compounds
N
NN
N
OR
OR
RO
RO
OO
OO
BenzeneH2N
H2N
OR
OR
+
1 2
3
3a, R = n-C10H21
3b, R = n-C11H23
3c, R = n-C14H29
3d, R =
3e, R =
Preparation of Target Compounds
Preparation of Target Compounds
Br
Br
Br
Br
OMe
OMe
MeO
MeO
OH
OH
HO
HO
O
O
O
O
CCl4
Br2
CH3OH
DMF, CuI
BBr3
CH2Cl2
O2
1
Synthesis of 4,5,9,10-Tetraone Pyrene
Synthesis of 4,5,9,10-Tetraone Pyrene
O2N
O2N
OCH3
OCH3
HBrO2N
O2N
OH
OH K2CO3, DMF
RBr
H2N
H2N
OR
OR
HCOO-NH4+
Pd/C, C2H5OH, THF
O2N
O2N
OR
OR
2
Synthesis of 4,5-Diamino-1,2-bisalkoxy Benzenes
Synthesis of 4,5-Diamino-1,2-bisalkoxy Benzenes
The transition temperatures (°C) were determined by DSC at 10 °C/min, the phase types were suggested by PLM and WAXD.
Compound R Phase transition
3a n-C10H21 K LC I
3b n-C11H23 K LC I
3c n-C14H29 K I
3d 2-methylhexyl K I
3e 3,7-dimethyloctyl K I
213 268
210 234
202
> 350
316
Phase Transition Compounds of 3a-e
Phase Transition Compounds of 3a-e
100 m
The picture was taken at 261The picture was taken at 261ooC cooling from C cooling from the isotropic phasethe isotropic phase
PLM Micrograph of 3aPLM Micrograph of 3a
Cyclic Voltammetry of C10 Discotic Liquid Crystal
in Dichlorobenzene w/ TBAF4 electrolyte
mV-1200 -1000 -800 -600 -400 -200 0
Cur
rent
, A
-2
0
2
4
6
8
E1/2 = -0.868 V vs AgCl
E1/2 = -1.065 V vs NHE
Square Wave Voltammetry of C10 Discotic Liquid Crystal
in Dichlorobenzene w/ TBAF4 electrolyte
mV
-1400 -1200 -1000 -800 -600 -400 -200 0
Cur
rent
, A
-2.4
-2.2
-2.0
-1.8
-1.6
-1.4
-1.2
-1.0
E1/2 = -0.874 V vs AgClE1/2 = -1.071 V vs NHE
Current WorkCurrent Work
Structural modifications to lower transition temperatures and
increase electron affinity.