Page 5 of 6
Journal of the American Chemical Society
(9) Pour, M. M.; Lashkov, A.; Radocea, A.; Liu, X.; Sun, T.; Lipatov,
(28) Wang, S.; Talirz, L.; Pignedoli, C. A.; Feng, X.; llen, K.; Fasel,
R.; Ruffieux, P. Giant edge state splitting at atomically precise graphene
zigzag edges. Nat. Commun. 2016, 7, 11507.
(29) Ma, C.; Xiao, Z.; Zhang, H.; Liang, L.; Huang, J.; Lu, W.; Sumpter,
B. G.; Hong, K.; Bernholc, J.; Li, A. P. Controllable conversion of
quasi-freestanding polymer chains to graphene nanoribbons. Nat. Com-
mun. 2017, 8, 14815.
(30) Sakaguchi, H.; Song, S.; Kojima, T.; Nakae, T. Homochiral
polymerization-driven selective growth of graphene nanoribbons. Nat.
Chem. 2017, 9, 57-63.
(31) Durr, R. A.; Haberer, D.; Lee, Y.; Blackwell, R.; Kalayjian, A. M.;
Marangoni, T.; Ihm, J.; Louie, S. G.; Fischer, F. R. Orbitally matched
edge-doping in graphene nanoribbons. J. Am. Chem. Soc. 2018, 140,
807-813.
(32) Pedramrazi, Z.; Chen, C.; Zhao, F.; Cao, T.; Nguyen, G. D.;
Omrani, A. A.; Tsai, H.; Cloke, R. R.; Marangoni, T.; Rizzo, D. J.;
Joshi, T.; Bronner, C.; Choi, W.; Fischer, F. R.; Louie, S. G.; M.
Crommie, F. Concentration dependence of dopant electronic structure in
bottom-up graphene nanoribbons. Nano Lett. 2018, 18, 3550-3556.
(33) Balagurusamy, V. S. K.; Ungar, G.; Percec, V.; Johansson, G.
Rational design of the first spherical supramolecular dendrimers self-
organized in a novel thermotropic cubic liquid-crystalline phase and the
determination of their shape by X-ray analysis. J. Am. Chem. Soc. 1997,
119, 1539-1555.
(34) Rao, K. V.; Miyajima, D.; Nihonyanagi, A.; Aida, T. Thermally
bisignate supramolecular polymerization. Nat. Chem. 2017, 9, 1133-
1139.
(35) Grayson, S. M.; Fréchet, J. M. J. Convergent dendrons and
dendrimers: from synthesis to applications. Chem. Rev. 2001, 101, 3819-
3868.
A.; Korlacki, R. A.; Shekhirev, M.; Aluru, N. R.; Lyding, J. W.; Sysoev,
V.; Sinitskii, A. Laterally extended atomically precise graphene
nanoribbons with improved electrical conductivity for efficient gas
sensing. Nat. Commun. 2017, 8, 820.
(10) Han, M.; zyilmaz, B.; Zhang, Y.; Kim, P. Energy band-gap engi-
neering of graphene nanoribbons. Phys. Rev. Lett. 2007, 98, 206805.
(11) Slota, M.; Keerthi, A.; Myers, W. K.; Tretyakov, E.; Baumgarten,
M.; Ardavan, A.; Sadeghi, H.; Lambert, C. J.; Narita, A.; Müllen, K.;
Bogani, L. Magnetic edge states and coherent manipulation of graphene
nanoribbons. Nature 2018, 557, 691-695.
(12) Huang, Y.; Mai, Y.; Yang, X.; Beser, U.; Liu, J.; Zhang, F.; Yan,
D.; llen, K.; Feng, X. Temperature-dependent multidimensional self-
assembly of polyphenylene-based “rod–coil” graft polymers. J. Am.
Chem. Soc. 2015, 137, 11602-11605.
(13) Huang, Y.; Mai, Y.; Beser, U.; Teyssandier, J.; Velpula, G.; Gorp,
H.; Hansen, L. A.; Hansen, M. R.; Rizzo, D.; Casiraghi, C.; Yang, R.;
Zhang, G.; Wu, D.; Zhang, F.; Yan, D.; Feyter, S. D.; llen, K.; Feng,
X. Poly (ethylene oxide) functionalized graphene nanoribbons with
excellent solution processability. J. Am. Chem. Soc. 2016, 138, 10136-
10139.
(14) Huang, Y.; Dou, W.; Xu, F.; Ru, H.; Gong, Q.; Wu, D.; Yan, D.;
Tian, H.; He, X.; Mai, Y.; Feng, X. Supramolecular nanostructures of
structurally defined graphene nanoribbons in the aqueous phase. Angew.
Chem. Int. Ed. 2018, 57, 3366-3371.
(15) Joshi, D.; Hauser, M.; Veber, G.; Berl, A.; Xu, K.; Fischer, F. R.
Super-resolution imaging of clickable graphene nanoribbons decorated
with fluorescent dyes. J. Am. Chem. Soc. 2018, 140, 9574-9580.
(16) Kosynkin, D. V.; Higginbotham, A. L.; Sinitskii, A.; Lomeda, J. R.;
Dimiev, A.; Price, B. K.; Tour, J. M. Longitudinal unzipping of carbon
nanotubes to form graphene nanoribbons. Nature 2009, 458, 872-876.
(17) Wang, X.; Dai, H. Etching and narrowing of graphene from the
edges. Nat. Chem. 2010, 2, 661-665.
1
2
3
4
5
6
7
8
9
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
(36) Schlüter, A. D.; Rabe, J. P. Dendronized polymers: synthesis,
characterization, assembly at interfaces, and manipulation. Angew.
Chem. Int. Ed. 2000, 39, 864-883.
(18) Schwab, M. G.; Narita, A.; Hernandez, Y.; Balandina, T.; Mali, K.
S.; Feyter, S. D.; Feng, X.; llen, K. Structurally defined graphene
nanoribbons with high lateral extension. J. Am. Chem. Soc. 2012, 134,
18169-18172.
(19) Daigle, M.; Miao, D.; Lucotti,A.; Tommasini,M.; Morin, J. F.
Helically coiled graphene nanoribbons. Angew. Chem. Int. Ed. 2017, 56,
6213-6217.
(20) Yang, W.; Lucotti, A.; Tommasini, M.; Chalifoux, W. A. Bottom-
up synthesis of soluble and narrow graphene nanoribbons using alkyne
benzannulations. J. Am. Chem. Soc. 2016, 138, 9137-9144.
(21) Dssel, L.; Gherghel, L.; Feng, X.; llen, K. Graphene
nanoribbons by chemists: nanometer-Sized, soluble, and defect-free.
Angew. Chem. Int. Ed. 2011, 50, 2540-2543.
(22) Huang, Y.; Xu, F.; Gan er, . amargo, . . A. Nagahara,T.
Teyssandier, . Gorp, . . asse, . traas , . A. Nagyte, .
asiraghi, . ansen, . R. eyter, . . an, . llen, K.; Feng,
X.; Cerullo, G.; Mai, Y. Intrinsic properties of single graphene
nanoribbons in solution: synthetic and spectroscopic studies. J. Am.
Chem. Soc. 2018, 140, 10416-10420.
(23) Miao, D.; Daigle, M.; Lucotti, A.; Boismenu-Lavoie, J.;
Tommasini, M.; Morin, J. F. Toward thiophene-annulated graphene
nanoribbons. Angew. Chem. Int. Ed. 2018, 57, 3588-3592.
(24) Li, G.; Yoon, K. Y.; Zhong, X.; Wang, J.; Zhang, R.; Guest, J. R.;
Wen, J.; Zhu, X. Y.; Dong, G.; A modular synthetic approach for band-
gap engineering of armchair graphene nanoribbons. Nat. Commun.
2018, 9, 1687.
(25) Hu, Y.; Xie, P.; Corato, M. D.; Ruini, A.; Zhao, S.; Meggendorfer,
F.; Straasø, L. A.; Rondin, L.; Simon, P.; Li, J.; Finley, J. J.; Hansen,
M. R.; Lauret, J. S.; Molinari, E.; Feng, X.; Barth, J. V.; Palma, C. A.;
Prezzi, D.; llen, K.; Narita, A. Bandgap engineering of graphene
nanoribbons by control over structural distortion. J. Am. Chem. Soc.
2018, 140, 7803-7809.
(26) Cai, J.; Ruffieux, P.; Jaafar, R.; Bieri, M.; Braun, T.; Blankenburg,
S.; Muoth, M.; Seitsonen, A. P.; Saleh, M.; Feng, X.; llen, K.; Fasel,
R. Atomically precise bottom-up fabrication of graphene nanoribbons.
Nature 2010, 466, 470-473.
(27) Chen,Y. C.; Cao, T.; Chen, C.; Pedramrazi, Z.; Haberer, D.;
Oteyza, D. G.; Fischer, F. R.; Louie, S. G.; Crommie, M. F. Molecular
bandgap engineering of bottom-up synthesized graphene nanoribbon
heterojunctions. Nat. Nanotechnol. 2015, 10, 156-160.
(37) (a) Zhang, S.; Cui, H.; Chen, Z.; Wooley, K. L.; Pochan, D. J. Helix
self-assembly through the coiling of cylindrical micelles. Soft Matter
2008, 4, 90-93; (b) Dupont, J.; Liu, G. J.; Niihara, K.; Kimoto, R.;
Jinnai, H. Self-assembled ABC triblock copolymer double and triple
helices. Angew. Chem. Int. Ed. 2009, 48, 6144-6147.
(38) Bae, J.; Choi, J.; Yoo, Y.; Oh, N.; Kim, B.; Lee, M. Helical nanofi-
bers from aqueous self-assembly of an oligo(p-phenylene)-based mo-
lecular dumbbell. J. Am. Chem. Soc. 2005, 127, 9668-9669.
(39) Ivanov, I.; Hu, Y. B.; Osella, S.; Beser, U.; Wang, H. I.; Beljonne,
D.; Narita, A.; Müllen, K.; Turchinovich, D.; Bonn, M. Role of edge
engineering in photoconductivity of graphene nanoribbons. J. Am.
Chem. Soc. 2017, 139, 7982-7988.
(40) Chen, Z. P.; Wang, H. I.; Teyssandier, J.; Mali, K. S.; Dumslaff, T.;
Ivanov, I.; Zhang, W.; Ruffieux, P.; Fasel, R.; Räder, H. J.; Turchino-
vich, D.; Feyter, S. D.; Feng, X.; Kläui, M.; Narita, A.; Bonn, M.;
Müllen, K. Chemical vapor deposition synthesis and terahertz photo-
conductivity of low-band-gap N = 9 armchair graphene nanoribbons. J.
Am. Chem. Soc. 2017, 139, 3635-3638.
(41) Chen, Z. P.; Wang, H. I.; Bilbao, N.; Teyssandier, J.; Prechtl, T.;
Cavani, N.; Tries, A.; Biagi, R.; Renzi, V. D.; Feng, X.; Kläui, M.;
Feyter, S. D.; Bonn, M.; Narita, A.; Müllen, K. Lateral fusion of chemi-
cal vapor deposited N = 5 armchair graphene nanoribbons. J. Am. Chem.
Soc. 2017, 139, 9483-9486.
(42) Jensen, S. A.; Ulbricht, R.; Narita, A.; Feng, X.; Müllen, K.; Hertel,
T.; Turchinovich, D.; Bonn, M. Ultrafast photoconductivity of graphene
nanoribbons and carbon nanotubes. Nano Lett. 2013, 13, 5925-5930.
(43) Narita, A.; Verzhbitskiy, I. A.; Frederickx, W.; Mali, K. S.; Jensen,
S. A.; Hansen, M. R.; Bonn, M.; S. Feyter, D.; Casiraghi, C.; Feng, X.;
Müllen, K. Bottom-up synthesis of liquid-phase-processable graphene
nanoribbons with near-infrared absorption. ACS Nano 2014, 8, 11622-
11630.
(44) Liu, Z. Y.; Wang, H. I.; Narita, A.; Chen, Q.; Mics, Z.; Turchino-
vich, D.; Kläui, M.; Bonn, M.; Müllen, K. Photoswitchable micro-
supercapacitor based on a diarylethene-graphene composite film. J. Am.
Chem. Soc. 2017, 139, 9443-9446.
(45) Ulbricht, R.; Hendry, E.; Shan, J.; Heinz, T. F.; Bonn, M. Carrier
dynamics in semiconductors studied with time-resolved terahertz spec-
troscopy. Rev. Mod. Phys. 2011, 83, 543.
(46) Wang, F.; Shan, J.; Islam, M. A.; Herman, I. P.; Bonn, M.; Heinz,
T. F. Exciton polarizability in semiconductor nanocrystals. Nat. Mater.
2006, 5, 861-864.
ACS Paragon Plus Environment