Rylene Ribbons with Unusual Diradical Character

Chem - Tập 2 - Trang 81-92 - 2017
Wangdong Zeng1, Hoa Phan1, Tun Seng Herng2, Tullimilli Y. Gopalakrishna1, Naoki Aratani3, Zebing Zeng4, Hiroko Yamada3, Jun Ding2, Jishan Wu1
1Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore
2Department of Materials Science & Engineering, National University of Singapore, Singapore 119260, Singapore
3Graduate School of Materials Science, Nara Institute of Science and Technology (NAIST), 8916-5 Takayama-cho, Ikoma 630-0192, Japan
4College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082, People's Republic of China

Tài liệu tham khảo

Li, 2008, Chemically derived, ultrasmooth graphene nanoribbon semiconductors, Science, 319, 1229, 10.1126/science.1150878 Koch, 2012, Voltage-dependent conductance of a single graphene nanoribbon, Nat. Nanotechnol., 7, 713, 10.1038/nnano.2012.169 Silveiro, 2015, Quantum nonlocal effects in individual and interacting graphene nanoribbons, Light. Sci. Appl., 4, e241, 10.1038/lsa.2015.14 Son, 2006, Half-metallic graphene nanoribbons, Nature, 444, 347, 10.1038/nature05180 Yazyev, 2010, Emergence of magnetism in graphene materials and nanostructures, Rep. Prog. Phys., 73, 056501, 10.1088/0034-4885/73/5/056501 Nakada, 1996, Edge state in graphene ribbons: nanometer size effect and edge shape dependence, Phys. Rev. B, 54, 17954, 10.1103/PhysRevB.54.17954 Wakabayashi, 1999, Electronic and magnetic properties of nanographite ribbons, Phys. Rev. B, 59, 8271, 10.1103/PhysRevB.59.8271 Son, 2006, Energy gaps in graphene nanoribbons, Phys. Rev. Lett., 97, 216803, 10.1103/PhysRevLett.97.216803 Barone, 2006, Electronic structure and stability of semiconducting graphene nanoribbons, Nano Lett., 6, 2748, 10.1021/nl0617033 Yazyev, 2013, A guide to the design of electronic properties of graphene nanoribbons, Acc. Chem. Res., 46, 2319, 10.1021/ar3001487 Chen, 2012, From nanographene and graphene nanoribbons to graphene sheets: chemical synthesis, Angew. Chem. Int. Ed. Engl., 51, 7640, 10.1002/anie.201201084 Wu, 2003, From branched polyphenylenes to graphite ribbons, Macromolecules, 36, 7082, 10.1021/ma0257752 Yang, 2008, Two-dimensional graphene nanoribbons, J. Am. Chem. Soc., 130, 4216, 10.1021/ja710234t Fogel, 2009, Graphitic nanoribbons with dibenzo[e,l]pyrene repeat units: synthesis and self-assembly, Macromolecules, 42, 6878, 10.1021/ma901142g Narita, 2013, Synthesis of structurally well-defined and liquid-phase-processable graphene nanoribbons, Nat. Chem., 6, 126, 10.1038/nchem.1819 Schwab, 2012, Structurally defined graphene nanoribbons with high lateral extension, J. Am. Chem. Soc., 134, 18169, 10.1021/ja307697j Vo, 2014, Large-scale solution synthesis of narrow graphene nanoribbons, Nat. Commun., 5, 3189, 10.1038/ncomms4189 Yang, 2016, Bottom-up synthesis of soluble and narrow graphene nanoribbons using alkyne benzannulations, J. Am. Chem. Soc., 138, 9137, 10.1021/jacs.6b03014 Ruffieux, 2016, On-surface synthesis of graphene nanoribbons with zigzag edge topology, Nature, 531, 489, 10.1038/nature17151 Yang, 2007, Quasiparticle energies and band gaps in graphene nanoribbons, Phys. Rev. Lett., 99, 186801, 10.1103/PhysRevLett.99.186801 Brey, 2006, Electronic states of graphene nanoribbons studied with the Dirac equation, Phys. Rev. B, 73, 235411, 10.1103/PhysRevB.73.235411 Ezawa, 2006, Peculiar width dependence of the electronic properties of carbon nanoribbons, Phys. Rev. B, 73, 045432, 10.1103/PhysRevB.73.045432 Cai, 2010, Atomically precise bottom-up fabrication of graphene nanoribbons, Nature, 466, 470, 10.1038/nature09211 Chen, 2013, Tuning the band gap of graphene nanoribbons synthesized from molecular precursors, ACS Nano, 7, 6123, 10.1021/nn401948e Zhang, 2015, On-surface synthesis of rylene-type graphene nanoribbons, J. Am. Chem. Soc., 137, 4022, 10.1021/ja511995r Kimouche, 2015, Ultra-narrow metallic armchair graphene nanoribbons, Nat. Commun., 6, 10177, 10.1038/ncomms10177 Konishi, 2010, Synthesis and characterization of teranthene: a singlet biradical polycyclic aromatic hydrocarbon having Kekule structures, J. Am. Chem. Soc., 132, 11021, 10.1021/ja1049737 Konishi, 2013, Synthesis and characterization of quarteranthene: elucidating the characteristics of the edge state of graphene nanoribbons at the molecular level, J. Am. Chem. Soc., 135, 1430, 10.1021/ja309599m Former, 2002, Cyclodehydrogenation of poly(perylene) to poly(quaterrylene): toward poly(peri-naphthalene), Macromolecules, 35, 1576, 10.1021/ma011724d Scholl, 1910, Perylen, ein hochkondensierter aromatischer Kohlenwasserstoff C20H12, Ber. Dtsch. Chem. Ges, 43, 2202, 10.1002/cber.191004302175 Markiewicz, 2015, Perylene, oligorylenes, and aza-Analogs, ACS Appl. Mater. Inter., 7, 28063, 10.1021/acsami.5b02243 Chen, 2014, Beyond perylene diimides: synthesis, assembly and function of higher rylene chromophores, J. Mater. Chem. C, 2, 1938, 10.1039/C3TC32315C Clar, 1948, Das Kondensationsprinzip, ein einfaches neues Prinzip im Aufbau der aromatischen Kohlenwassorstoffe (Aromatische Kohlenwasserstoffe, XLII. Mitteilung), Chem. Ber., 81, 52, 10.1002/cber.19480810110 Clar, 1956, Die synthesen des terrylens und quaterrylens und über das vermeintliehe quaterrylen von A, Zinke. Monatsh. Chem., 87, 391, 10.1007/BF00902634 Bohnen, 1990, Oligorylene as a model for “poly(peri-naphthalene)”, Angew. Chem. Int. Ed. Engl., 29, 525, 10.1002/anie.199005251 Koch, 1991, Synthesis of tetraalkyl-substituted oligo(l,4-naphthylene)s and cyclization to soluble oligo(peri-naphthylene), Chem. Ber., 124, 2091, 10.1002/cber.19911240935 Holtrup, 1997, Terrylenimides: new NIR fluorescent dyes, Chem. Eur. J., 3, 219, 10.1002/chem.19970030209 Quante, 1995, Quaterrylenebis(dicarboximides), Angew. Chem. Int. Ed. Engl., 34, 1323, 10.1002/anie.199513231 Pschirer, 2006, Pentarylene- and hexarylenebis(dicarboximide)s: near-infrared-absorbing polyaromatic dyes, Angew. Chem. Int. Ed. Engl., 45, 1401, 10.1002/anie.200502998 Yuan, 2013, Processable rylene diimide dyes up to 4 nm in length: synthesis and STM visualization, Chem. Eur. J., 19, 11842, 10.1002/chem.201302086 Li, 2009, Bis-N-annulated quaterrylene: an approach to processable graphene nanoribbons, Org. Lett., 11, 1385, 10.1021/ol9002064 Li, 2010, Tri-N-annulated hexarylene: an approach to well-defined graphene nanoribbons with large dipoles, J. Am. Chem. Soc., 132, 4208, 10.1021/ja100276x Jiao, 2009, Bis-N-annulated quaterrylenebis(dicarboximide) as a new soluble and stable near-infrared dye, Org. Lett., 11, 4508, 10.1021/ol902027b Zeng, 2013, Pushing extended p-quinodimethanes to the limit: stable tetracyano-oligo(N-annulated perylene)quinodimethanes with tunable ground states, J. Am. Chem. Soc., 135, 6363, 10.1021/ja402467y Zeng, 2013, Tetracyano- quaterrylene and hexarylenequinodimethanes with tunable ground states and strong near-infrared absorption, Angew. Chem. Int. Ed. Engl., 52, 8561, 10.1002/anie.201305348 Zeng, 2015, Push−pull type oligo(N-annulated perylene)quinodimethanes: chain length and solvent-dependent ground states and physical properties, J. Am. Chem. Soc., 137, 8572, 10.1021/jacs.5b04156 Zeng, 2015, Cyclopenta-fused perylene: a new soluble, stable and functionalizable rylene building block, Sci. Bull., 60, 1266, 10.1007/s11434-015-0839-3 Tsuda, 2001, Fully conjugated porphyrin tapes with electronic absorption bands that reach into infrared, Science, 293, 79, 10.1126/science.1059552 Tsuda, 2002, Discrete conjugated porphyrin tapes with an exceptionally small bandgap, Adv. Mater., 14, 75, 10.1002/1521-4095(20020104)14:1<75::AID-ADMA75>3.0.CO;2-8 Abe, 2013, Diradicals, Chem. Rev., 113, 7011, 10.1021/cr400056a Sun, 2014, Zethrenes, extended p-quinodimethanes, and periacenes with a singlet biradical ground state, Acc. Chem. Res., 47, 2582, 10.1021/ar5001692 Zeng, 2015, Pro-aromatic and anti-aromatic π-conjugated molecules: an irresistible wish to be diradicals, Chem. Soc. Rev., 44, 6578, 10.1039/C5CS00051C Motta, 2010, Biradicaloid and polyenic character of quinoidal oligothiophenes revealed by the presence of a low-lying double-exciton state, J. Phys. Chem. Lett., 1, 3334, 10.1021/jz101400d Brédas, 1993, Chain-length dependence of electronic and electrochemical properties of conjugated systems: polyacetylene, polyphenylene, polythiophene, and polypyrrole, J. Am. Chem. Soc., 105, 6555, 10.1021/ja00360a004 Minami, 2012, Theoretical study of singlet fission in oligorylenes, J. Phys. Chem. Lett., 3, 2719, 10.1021/jz3011749 Sun, 2013, Dibenzoheptazethrene isomers with different biradical characters: an exercise of Clar’s aromatic sextet rule in singlet biradicaloids, J. Am. Chem. Soc., 135, 18229, 10.1021/ja410279j Coulson, 1940, Note on the method of molecular orbitals, Proc. Cambridge. Philos. Soc., 36, 193, 10.1017/S0305004100017163 Mallion, 1990, The golden jubilee of the Coulson-Rushbrooke pairing theorem, J. Math. Chem., 5, 1, 10.1007/BF01166272