TY - JOUR
T1 - Long, Atomically Precise Donor-Acceptor Cove-Edge Nanoribbons as Electron Acceptors
AU - Sisto, Thomas J.
AU - Zhong, Yu
AU - Zhang, Boyuan
AU - Trinh, M. Tuan
AU - Miyata, Kiyoshi
AU - Zhong, Xinjue
AU - Zhu, X. Y.
AU - Steigerwald, Michael L.
AU - Ng, Fay
AU - Nuckolls, Colin
N1 - Funding Information:
C.N. thanks Sheldon and Dorothea Buckler for their generous support. Primary support for this project was provided by the Chemical Sciences, Geosciences and Biosciences Division, Office of Basic Energy Sciences, U.S. Department of Energy (DOE), under award no. DE-FG02-01ER15264 for synthesis and device characterization. Partial support was provided by the Office of Naval Research under award no. N00014-16-1-2921. X.-Y.Z. and C.N. acknowledge the U.S. Department of Energy grant DE-SC0014563 for the transient absorption experiments and the Center for Precision Assembly of Superstratic and Superatomic Solids supported by the National Science Foundation (NSF) grant DMR-1420634 for the AFM imaging experiment. We graciously thank Ryan Hastie for help with the TOC graphic. The Columbia University Shared Materials Characterization Laboratory (SMCL) was used extensively for this research. We are grateful to Columbia University for support of this facility.
Publisher Copyright:
© 2017 American Chemical Society.
PY - 2017/4/26
Y1 - 2017/4/26
N2 - This Communication describes a new molecular design for the efficient synthesis of donor-acceptor, cove-edge graphene nanoribbons and their properties in solar cells. These nanoribbons are long (∼5 nm), atomically precise, and soluble. The design is based on the fusion of electron deficient perylene diimide oligomers with an electron rich alkoxy pyrene subunit. This strategy of alternating electron rich and electron poor units facilitates a visible light fusion reaction in >95% yield, whereas the cove-edge nature of these nanoribbons results in a high degree of twisting along the long axis. The rigidity of the backbone yields a sharp longest wavelength absorption edge. These nanoribbons are exceptional electron acceptors, and organic photovoltaics fabricated with the ribbons show efficiencies of ∼8% without optimization.
AB - This Communication describes a new molecular design for the efficient synthesis of donor-acceptor, cove-edge graphene nanoribbons and their properties in solar cells. These nanoribbons are long (∼5 nm), atomically precise, and soluble. The design is based on the fusion of electron deficient perylene diimide oligomers with an electron rich alkoxy pyrene subunit. This strategy of alternating electron rich and electron poor units facilitates a visible light fusion reaction in >95% yield, whereas the cove-edge nature of these nanoribbons results in a high degree of twisting along the long axis. The rigidity of the backbone yields a sharp longest wavelength absorption edge. These nanoribbons are exceptional electron acceptors, and organic photovoltaics fabricated with the ribbons show efficiencies of ∼8% without optimization.
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U2 - 10.1021/jacs.6b13093
DO - 10.1021/jacs.6b13093
M3 - Article
C2 - 28418665
AN - SCOPUS:85018358498
SN - 0002-7863
VL - 139
SP - 5648
EP - 5651
JO - Journal of the American Chemical Society
JF - Journal of the American Chemical Society
IS - 16
ER -