Page 5 of 6
Journal of the American Chemical Society
Author Contributions
1
2
‡ J.L. and E.G contributed equally.
3
4
Notes
The authors declare no competing financial interest.
5
6
7
ACKNOWLEDGMENT
8
9
The authors thank the MRSEC program of the National
Science Foundation (DMR 1121053, C.J.H.), the Dow
Chemical Company through the Dow Materials Insti-
tute at UCSB (J.L., C.J.H.), and the Institute for Collabo-
rative Biotechnologies through grant W911NF-09-0001
from the U.S. Army Research Office (C.J.H.). The con-
tent of the information does not necessarily reflect the
position or the policy of the U.S. government, and no
official endorsement should be inferred. E.G. thanks
the support by Grant-in-Aid from JSPS, Research Fel-
lowship for Young Scientists (15J00430) and Innovative
Flex Course for Frontier Organic Material Systems
(iFront) at Yamagata University. J.M.R. thanks the Vic-
torian Endowment for Science, Knowledge and Innova-
tion (VESKI) for a postdoctoral fellowship.
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
Figure 6. Top: asymmetric and symmetric donor-
acceptor materials, D8A, D6AD2 and D4AD4 (D=3-
hexylthiophene, A=benzothiadiazole). Bottom: UV-vis
and PL spectra of D8A (black), D6AD2 (blue) and
D4AD4 (red).
REFERENCES
1.
Patil, A. O.; Heeger, A. J.; Wudl, F., Chem. Rev. 1988, 88
CONCLUSION
(1), 183-200.
2.
Sivula, K.; Luscombe, C. K.; Thompson, B. C.; Fréchet,
In summary, the combination of controlled
polymerization and automated chromatographic
separation represents a highly efficient and powerful
approach to the preparation of discrete conjugated
oligomer libraries. The increased availability of dif-
ferent conjugated oligomers with high structural pu-
rity and in synthetically useful quantities offers un-
precedented opportunities for tuning electronic and
photonic properties. By simple mixing of discrete
oligomers (e.g., all-thiophene mixture) or preparing
novel materials with unique monomer sequence,
dramatic changes in photoluminescence is achieved,
illustrating the significant potential of these discrete
conjugated building blocks for designer materials
and nanoscale assemblies.
J. M. J., J. Am. Chem. Soc. 2006, 128 (43), 13988-13989.
3.
Fichou, D., Handbook of oligo-and polythiophenes. John
Wiley & Sons: 2008.
4.
Beaujuge, P. M.; Frechet, J. M., J. Am. Chem. Soc. 2011,
133 (50), 20009-29.
5.
6.
Facchetti, A., Chem. Mater. 2011, 23 (3), 733-758.
Ardoña, H. A. M.; Tovar, J. D., Bioconjugate Chem.
2015, 26 (12), 2290-2302.
7.
Chen, T.; Wu, X.; Rieke, R. D., J. Am. Chem. Soc. 1995,
117 (1), 233-244.
8.
Sheina, E. E.; Liu, J. S.; Iovu, M. C.; Laird, D. W.;
McCullough, R. D., Macromolecules 2004, 37 (10), 3526-3528.
9.
Yokoyama, A.; Miyakoshi, R.; Yokozawa, T.,
Macromolecules 2004, 37 (4), 1169-1171.
10.
Iovu, M. C.; Sheina, E. E.; Gil, R. R.; McCullough, R. D.,
Macromolecules 2005, 38 (21), 8649-8656.
11.
Miyakoshi, R.; Yokoyama, A.; Yokozawa, T., J. Am.
Chem. Soc. 2005, 127 (49), 17542-17547.
12.
Kline, R. J.; McGehee, M. D.; Kadnikova, E. N.; Liu, J.;
Fréchet, J. M. J., Adv. Mater. 2003, 15 (18), 1519-1522.
ASSOCIATED CONTENT
13.
G.; Allard, S.; Scherf, U., Appl. Phys. A 2008, 95 (1), 67-72.
14. Himmelberger, S.; Vandewal, K.; Fei, Z.; Heeney, M.;
Salleo, A., Macromolecules 2014, 47 (20), 7151-7157.
15. Meier, H.; Stalmach, U.; Kolshorn, H., Acta Polym.
1997, 48 (9), 379-384.
Pingel, P.; Zen, A.; Neher, D.; Lieberwirth, I.; Wegner,
Supporting Information.
Experimental procedures and characterization data for
all compounds (PDF). The Supporting Information is
available free of charge via the Internet at
16.
Martin, R. E.; Diederich, F., Angew. Chem. Int. Ed.
1999, 38 (10), 1350-1377.
AUTHOR INFORMATION
17.
Brown, P. J.; Thomas, D. S.; Köhler, A.; Wilson, J. S.;
Kim, J.-S.; Ramsdale, C. M.; Sirringhaus, H.; Friend, R. H., Phys.
Rev. B. 2003, 67 (6), 064203.
Corresponding Author
*hawker@mrl.ucsb.edu
ACS Paragon Plus Environment