Design and Synthesis of Novel Pyrene Discotics and Their Investigation in Organic Photovoltaic Cells Bilal R. Kaafarani, Department of Chemistry, American University of Beirut, Beirut, Lebanon
K2 Phase Y
K3 Phase
X
N
N
X
X
N
N
X
Y TQPP-[Y]2-[X]4
K4 Phase
Y=
, X = SPhytanyl
S
Y=
, X = SC12H25
S
Y=
, X = SPhytanyl
S
TQPP-[4-t-Bu-phenyl]2-[SPhytanyl]4 heating
st
1 heating
0.4 0.2 0.0 -0.2
39 ºC 120 ºC
4
10
3
10
intensity (counts)
2
17
0.6
intensity (counts)
exothermic heat (mW)
0.8
nd
15 ºC 120 ºC
4
10
3
10
st
1 cooling
-0.4 -0.6
2
2
10 -50
0
50
100
150
10
5
200
10
15 2θ (º)
20
25
5
10
15
2θ (º)
20
25
Temperature (ºC)
Y
X
Phase transitions (heating)
Phase transitions (cooling)
100
Mass (%)
98
p-t-Buphenyl
96
94
104.7 ºC a 239 ºC b sK Colh I -19.53 KJ/mol
TQPP-[t-Bu]2-[SC12H25]4 TQPP-[t-Bu]2-[SPhytanyl]4 TQPP-[4-t-Bu-phenyl]2-[SPhytanyl]4
225
250
275
T (°C)
300
233 ºCb I
21.2 ºC Colrc Colh 6.13 KJ/mol
41.0 ºC Colrc
92
90 200
SPhytanyl
325
350
a
Colh -6.98 KJ/mol
Transition was only observed in the first heating run. b Transition was determined by POM. c Preliminary phase assignments.
