Paper
Journal of Materials Chemistry C
1
1 mmol) were placed in a dry Schlenk flask and de-gassed with and start up funds from the Colorado School of Mines (AS). We
vacuum and back-filling with inert gas, three times. Toluene thank Prof. Alberto Salleo and Ms Camila Arantxa Cendra
5 mL) was added and the reaction heated at 80 1C for 3 days. Guinassi from Stanford University, Department of Materials
(
The reaction was then poured into excess 5% HCl in MeOH (v/v) Science and Engineering for their help in testing these materials
and collected by filtration. This solid was then suspended in in organic field-effect transistors (OFETs). The Advanced Light
DCM and filtered, and the filtrate concentrated to yield a brick- Source is supported by the Director, Office of Science, Office of
1
red powder (56 mg, 21%). H NMR (500 MHz, CDCl
3
): d 8.86 Basic Energy Sciences of the U.S. Department of Energy under
(
(
(
(
d, 2H, J = 8.00 Hz), 8.82 (s, 2H), 8.68 (d, 2H, J = 8.25 Hz), 8.21 Contract No. DE-AC02-05CH11231. Crystallographic data for the
s, 2H), 8.16 (d, 2H, J = 16.00 Hz), 7.99 (t, 2H, J = 7.80 Hz), 7.92 structures reported in this paper have been deposited with the
s, 4H), 7.60 (d, 2H, J = 16.05 Hz), 3.64 (d, 4H, J = 7.30 Hz), 1.91 CCDC 1526927 and 1526928.†
m, 2H), 1.37 (m, 4H), 1.27 (m, 64H), 0.89 (t, 12H, J = 14 Hz).
ꢁ
MALDI-TOF: C H N O (calc. 1209.68) found 1210.67 [M ] m/z.
82 100 2 6
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,10-Bis(5-hexylbithiophen-2 -yl)anthanthrone (8)
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2
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Acknowledgements
This work was partially supported by funds provided by the
Global Climate and Energy Project (GCEP) award # 1138721 and 18 R. Cardia, G. Malloci, A. Mattoni and G. Cappellini, J. Phys.
by the Center for Advanced Molecular Photovoltaics (CAMP), Chem. A, 2014, 118, 5170–5177.
award # KUS-C1-015-21 made by the King Abdullah University 19 A. N. Simonov, P. Kemppinen, C. Pozo-Gonzalo, J. F. Boas,
of Science and Technology (KAUST). Funding was also provided
by the Research Corporation for Science Advancement (RCSA)
through the Scialog Collaborative Innovation Award (#22355),
A. Bilic, A. D. Scully, A. Attia, A. Nafady, E. A. Mashkina,
K. N. Winzenberg, S. E. Watkins and A. M. Bond, J. Phys.
Chem. B, 2014, 118, 6839–6849.
J. Mater. Chem. C
This journal is ©The Royal Society of Chemistry 2017