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Fully Conjugated Tri(perylene bisimides): An Approach to the Construction of n-Type Graphene Nanoribbons

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Beijing National Laboratory for Molecular Sciences, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China, Dipartimento di Chimica “G. Ciamician”, Unversità di Bologna, Via F. Selmi 2, 40126 Bologna, Italy and INSTM, UdR Bologna, Italy, and Graduate School of the Chinese Academy of Sciences, Beijing 100190, China
†Institute of Chemistry, Chinese Academy of Sciences.
§Graduate School of the Chinese Academy of Sciences.
‡Unversità di Bologna and INSTM.
Cite this: J. Am. Chem. Soc. 2008, 130, 52, 17970–17976
Publication Date (Web):November 26, 2008
https://doi.org/10.1021/ja807803j
Copyright © 2008 American Chemical Society

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    Abstract

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    We present an experimental study encompassing synthesis and characterization of fully conjugated tri(perylene bisimides) (triPBIs), having 19 six-membered carbon rings in the core and six imide groups at the edges. Two structural isomers of triPBIs resulting from the two probable coupling positions were successfully separated by HPLC. To assist the identification of the two structural isomers, quantum-chemical calculations of electronic structure, NMR, and optical spectra were carried out. Calculations predict stable helical and nonhelical configurations for both triPBIs isomers and allow the assignment of triPBIs 6 unequivocally to the most bathochromically shifted absorption spectrum. Increasing the number of PBI units in oligo-PBIs leads to an expansion of the π system, in turn associated with a reduction of the transport and optical band gaps, and a remarkable increase in electron affinities, which make oligo-PBIs promising n-type functional components in optoelectronic devices.

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    Complete ref 17, experimental section, MS, 1H and 13C NMR spectra, DPV of 5 and 6, optimized structures of 1 and 4, comparison between computed and experimental absorption spectra of 4, and tables with MO energies, absolute energies, and optical and transport gaps. This information is available free of charge via the Internet at http://pubs.acs.org.

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    11. Xinliang Zhang, Bo Jiang, Xin Zhang, Ailing Tang, Jianhua Huang, Chuanlang Zhan, and Jiannian Yao . Cooperatively Tuning Phase Size and Absorption of Near IR Photons in P3HT:Perylene Diimide Solar Cells by Bay-Modifications on the Acceptor. The Journal of Physical Chemistry C 2014, 118 (42) , 24212-24220. https://doi.org/10.1021/jp5093674
    12. Wei Jiang, Yan Li, and Zhaohui Wang . Tailor-Made Rylene Arrays for High Performance n-Channel Semiconductors. Accounts of Chemical Research 2014, 47 (10) , 3135-3147. https://doi.org/10.1021/ar500240e
    13. Yu Zhong, Bharat Kumar, Seokjoon Oh, M. Tuan Trinh, Ying Wu, Katherine Elbert, Panpan Li, Xiaoyang Zhu, Shengxiong Xiao, Fay Ng, Michael L. Steigerwald, and Colin Nuckolls . Helical Ribbons for Molecular Electronics. Journal of the American Chemical Society 2014, 136 (22) , 8122-8130. https://doi.org/10.1021/ja503533y
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    15. Jing Gao, Chengyi Xiao, Wei Jiang, and Zhaohui Wang . Cyano-Substituted Perylene Diimides with Linearly Correlated LUMO Levels. Organic Letters 2014, 16 (2) , 394-397. https://doi.org/10.1021/ol403250r
    16. Amanda V. Ellis, Altaf Al-deen, Habibullah Dalal, and Gunther G. Andersson . Structural Determination of Thermally and Hydrazine Treated Graphene Oxide Using Electron Spectroscopic Analysis. The Journal of Physical Chemistry C 2013, 117 (41) , 21312-21319. https://doi.org/10.1021/jp405682u
    17. Xin Tan and Peter Zapol . Regioselective Oxidation of Strained Graphene for Controllable Synthesis of Nanoribbons. The Journal of Physical Chemistry C 2013, 117 (37) , 19160-19166. https://doi.org/10.1021/jp402312k
    18. Lin Zou, Xiao-Ye Wang, Ke Shi, Jie-Yu Wang, and Jian Pei . Fusion at the Non-K-Region of Pyrene: An Alternative Strategy To Extend the π-Conjugated Plane of Pyrene. Organic Letters 2013, 15 (17) , 4378-4381. https://doi.org/10.1021/ol401904n
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    73. Jian-Long Xu, Rui-Xuan Dai, Yan Xin, Yi-Lin Sun, Xian Li, Yang-Xin Yu, Lan Xiang, Dan Xie, Sui-Dong Wang, Tian-Ling Ren. Efficient and Reversible Electron Doping of Semiconductor-Enriched Single-Walled Carbon Nanotubes by Using Decamethylcobaltocene. Scientific Reports 2017, 7 (1) https://doi.org/10.1038/s41598-017-05967-w
    74. Sabine Seifert, David Schmidt, Kazutaka Shoyama, Frank Würthner. Base‐Selective Five‐ versus Six‐Membered Ring Annulation in Palladium‐Catalyzed C–C Coupling Cascade Reactions: New Access to Electron‐Poor Polycyclic Aromatic Dicarboximides. Angewandte Chemie 2017, 129 (26) , 7703-7708. https://doi.org/10.1002/ange.201702889
    75. Sabine Seifert, David Schmidt, Kazutaka Shoyama, Frank Würthner. Base‐Selective Five‐ versus Six‐Membered Ring Annulation in Palladium‐Catalyzed C–C Coupling Cascade Reactions: New Access to Electron‐Poor Polycyclic Aromatic Dicarboximides. Angewandte Chemie International Edition 2017, 56 (26) , 7595-7600. https://doi.org/10.1002/anie.201702889
    76. Meizhuang Liu, Mengxi Liu, Limin She, Zeqi Zha, Jinliang Pan, Shichao Li, Tao Li, Yangyong He, Zeying Cai, Jiaobing Wang, Yue Zheng, Xiaohui Qiu, Dingyong Zhong. Graphene-like nanoribbons periodically embedded with four- and eight-membered rings. Nature Communications 2017, 8 (1) https://doi.org/10.1038/ncomms14924
    77. Jonathan Cann, Sergey Dayneko, Jon-Paul Sun, Arthur D. Hendsbee, Ian G. Hill, Gregory C. Welch. N-Annulated perylene diimide dimers: acetylene linkers as a strategy for controlling structural conformation and the impact on physical, electronic, optical and photovoltaic properties. Journal of Materials Chemistry C 2017, 5 (8) , 2074-2083. https://doi.org/10.1039/C6TC05107C
    78. Wenxuan Mao, Junji Zhang, Xin Li, Chen Li, He Tian. Regioisomerically pure multiaryl coronene derivatives: highly efficient synthesis via bay-extended perylene tetrabutylester. Chemical Communications 2017, 53 (36) , 5052-5055. https://doi.org/10.1039/C7CC02803B
    79. Xiangchun Li, Hengbin Wang, Julia A. Schneider, Zitang Wei, Wen-Yong Lai, Wei Huang, Fred Wudl, Yonghao Zheng. Catalyst-free one-step synthesis of ortho-tetraaryl perylene diimides for efficient OPV non-fullerene acceptors. Journal of Materials Chemistry C 2017, 5 (11) , 2781-2785. https://doi.org/10.1039/C7TC00263G
    80. Helin Wang, Lingcheng Chen, Yi Xiao. Heterologous perylene diimide arrays: potential non-fullerene acceptors in organic solar cells. Journal of Materials Chemistry C 2017, 5 (34) , 8875-8882. https://doi.org/10.1039/C7TC03171H
    81. Helin Wang, Lingcheng Chen, Yi Xiao. Perylene diimide arrays: promising candidates for non-fullerene organic solar cells. Journal of Materials Chemistry C 2017, 5 (48) , 12816-12824. https://doi.org/10.1039/C7TC04726F
    82. Zhi Lin, Cheng Li, Dong Meng, Yan Li, Zhaohui Wang. Hybrid Corannulene–Perylene Dyes: Facile Synthesis and Optoelectronic Properties. Chemistry – An Asian Journal 2016, 11 (19) , 2695-2699. https://doi.org/10.1002/asia.201600490
    83. Sabine Seifert, Kazutaka Shoyama, David Schmidt, Frank Würthner. An Electron‐Poor C 64 Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis. Angewandte Chemie 2016, 128 (22) , 6500-6505. https://doi.org/10.1002/ange.201601433
    84. Sabine Seifert, Kazutaka Shoyama, David Schmidt, Frank Würthner. An Electron‐Poor C 64 Nanographene by Palladium‐Catalyzed Cascade C−C Bond Formation: One‐Pot Synthesis and Single‐Crystal Structure Analysis. Angewandte Chemie International Edition 2016, 55 (22) , 6390-6395. https://doi.org/10.1002/anie.201601433
    85. Cheng Li, Zhi Lin, Yan Li, Zhaohui Wang. Synthesis and Applications of π-Extended Naphthalene Diimides. The Chemical Record 2016, 16 (2) , 873-885. https://doi.org/10.1002/tcr.201500246
    86. Tianfei Ren, Xiaoxiao Shen, Lingui Han, Libin Bai, Hongchi Zhao, Yonggang Wu, Haijun Wang, Xinwu Ba. Ladder-Type Perylene Diimides Linked by Pyrene Bridges at Bay Area. ChemistrySelect 2016, 1 (2) , 267-271. https://doi.org/10.1002/slct.201500034
    87. Patrick E. Hartnett, H. S. S. Ramakrishna Matte, Nicholas D. Eastham, Nicholas E. Jackson, Yilei Wu, Lin X. Chen, Mark A. Ratner, Robert P. H. Chang, Mark C. Hersam, Michael R. Wasielewski, Tobin J. Marks. Ring-fusion as a perylenediimide dimer design concept for high-performance non-fullerene organic photovoltaic acceptors. Chemical Science 2016, 7 (6) , 3543-3555. https://doi.org/10.1039/C5SC04956C
    88. Xiaoping Cui, Chengyi Xiao, Lei Zhang, Yan Li, Zhaohui Wang. Polycyclic aromatic hydrocarbons with orthogonal tetraimides as n-type semiconductors. Chemical Communications 2016, 52 (90) , 13209-13212. https://doi.org/10.1039/C6CC06486H
    89. Cheng Zeng, Chengyi Xiao, Rui Xin, Wei Jiang, Yafei Wang, Zhaohui Wang. Influence of alkyl chain branching point on the electron transport properties of di(perylene diimides) thin film transistors. RSC Advances 2016, 6 (61) , 55946-55952. https://doi.org/10.1039/C6RA09781B
    90. Jing Li, Shen-Yuan Yang, Shu-Shen Li. N-Doped Zigzag Graphene Nanoribbons on Si(001): a First-Principles Calculation. Chinese Physics Letters 2015, 32 (7) , 077102. https://doi.org/10.1088/0256-307X/32/7/077102
    91. Takeshi Maeda, Frank Würthner. Halochromic and hydrochromic squaric acid functionalized perylene bisimide. Chemical Communications 2015, 51 (36) , 7661-7664. https://doi.org/10.1039/C5CC01691F
    92. Chong Zhu, Siwei Yang, Gang Wang, Runwei Mo, Peng He, Jing Sun, Zengfeng Di, Ningyi Yuan, Jianning Ding, Guqiao Ding, Xiaoming Xie. Negative induction effect of graphite N on graphene quantum dots: tunable band gap photoluminescence. Journal of Materials Chemistry C 2015, 3 (34) , 8810-8816. https://doi.org/10.1039/C5TC01933H
    93. Glauco Battagliarin, Sreenivasa Reddy Puniredd, Sebastian Stappert, Wojciech Zajaczkowski, Suhao Wang, Chen Li, Wojciech Pisula, Klaus Müllen. Ortho ‐ vs Bay ‐Functionalization: A Comparative Study on Tetracyano‐Terrylenediimides. Advanced Functional Materials 2014, 24 (47) , 7530-7537. https://doi.org/10.1002/adfm.201401573
    94. Chaolumen, Hiroki Enno, Michihisa Murata, Atsushi Wakamiya, Yasujiro Murata. Dibenzo[ a , f ]perylene Bisimide: Effects of Introducing Two Fused Rings. Chemistry – An Asian Journal 2014, 9 (11) , 3136-3140. https://doi.org/10.1002/asia.201402688
    95. Yexuan Mao, Qiannan Fan, Jianjun Li, Lanlan Yu, Ling-bo Qu. A novel and green CTAB-functionalized graphene nanosheets electrochemical sensor for Sudan I determination. Sensors and Actuators B: Chemical 2014, 203 , 759-765. https://doi.org/10.1016/j.snb.2014.07.024
    96. Youdi Zhang, Lingcheng Chen, Kaichen Zhang, Helin Wang, Yi Xiao. A Soluble Ladder‐Conjugated Star‐Shaped Oligomer Composed of Four Perylene Diimide Branches and a Fluorene Core: Synthesis and Properties. Chemistry – A European Journal 2014, 20 (32) , 10170-10178. https://doi.org/10.1002/chem.201402100
    97. Bernard Pagoaga, Louis Giraudet, Norbert Hoffmann. Synthesis and Characterisation of 1,7‐Di‐ and Inherently Chiral 1,12‐Di‐ and 1,6,7,12‐Tetraarylperylenetetracarbox‐3,4:9,10‐diimides. European Journal of Organic Chemistry 2014, 2014 (24) , 5178-5195. https://doi.org/10.1002/ejoc.201402625
    98. Wan Yue, Wei Jiang, Marcus Böckmann, Nikos L. Doltsinis, Zhaohui Wang. Regioselective Functionalization of Core‐Persubstituted Perylene Diimides. Chemistry – A European Journal 2014, 20 (18) , 5209-5213. https://doi.org/10.1002/chem.201400397
    99. Bostjan Genorio, Andrej Znidarsic. Functionalization of graphene nanoribbons. Journal of Physics D: Applied Physics 2014, 47 (9) , 094012. https://doi.org/10.1088/0022-3727/47/9/094012
    100. Wei Jiang, Long Ye, Xiangguang Li, Chengyi Xiao, Fang Tan, Wenchao Zhao, Jianhui Hou, Zhaohui Wang. Bay-linked perylene bisimides as promising non-fullerene acceptors for organic solar cells. Chem. Commun. 2014, 50 (8) , 1024-1026. https://doi.org/10.1039/C3CC47204C
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