Theoretical study on the electronic structures and photophysical properties of carbon nanorings and their analogues

Xu Ying-Ying; Kan Yu-He; Wu Jie; Tao Wei; Su Zhong-Min

doi:10.7498/aps.62.083101

Abstract

Density functional theory (DFT) is used in a series of hexacene nanoring ([6]CA), its boron nitride analogue ([6]CA-BN) and lithium ion doping derivatives to obtain an insight into electronic structure, aromaticity property, energy gap, ionization potential, electron affinity and reorganization energy. DFT calculations of these nanorings indicate that the energy gaps of the carbon nanorings are smaller than those of the boron nitride nanorings. The lithium ion doping will remarkably reduce the HOMO and LUMO energy. The aromaticities of the rings are investigated though nucleus-independent chemical shift (NICS) values. The NICS scan suggests that the aromaticities of carbon nanoring systems are more than those of boron nitride analogues, the aromaticities of boron nitride compounds are very weak due to orbital localization. We also calculate the reorganization energy to investigate the charge transport properties. The results show that the carbon nanoring and their analogues could serve as bipolar carrier transport materials in photoelectric functional materials, and the lithium ion doping significantly improves the charge transport properties. The [6]CA-BN nanorings serve as better electron-transport materials. Furthermore, the lithium ion doping significantly affects the charge transfer property of [6]CA-BN nanoring, making it used as bipolar carrier transport materials. The time dependant DFT investigations show that the boron nitride substitution leads to an important change in absorption spectrum with blue-shift. And lithium ion doping has no obvious influence on absorption spectrum.

Keywords:

Authors and contacts

1.
Jiangsu Province Key Laboratory for Chemistry of Low-Dimensional Materials, School of Chemistry and Chemical Engineering, Huaiyin NormalUniversity, Huaian 223300, China;
2.
Institute of Functional Material Chemistry, Faculty of Chemistry, Northeast Normal University, Changchun 130024, China
Funds: Project supported by the National Basic Research Program of China (Grant No. 2009CB623605), the National Natural Science Foundation of China (Grant No. 21273030), the Natural Science Foundation of Jiangsu Province, China (Grant No. BK2011408), the Opening Project of Key Laboratory for Chemistry of Low-Dimensional Materials of Jiangsu Province, China (Grant No. JSKC12109), and the Cultivation Fund of the Key Scientific Innovation Project of Huaiyin Normal University, China (Grant No. 11HSGJBZ11).

References

[1]	Iijima S 1991 Nature 354 56
[2]	Prasek J, Drbohlavova J, Chomoucka J, Hubalek J, Jasek O, Adam V, Kizek R 2011 J. Mater. Chem. 21 15872
[3]	Omachi H, Segawa Y, Itami K 2012 Acc. Chem. Res. 45 1378
[4]	Kawase T, Kurata H 2006 Chem. Rev. 106 5250
[5]	Scott L T 2003 Angew. Chem. Int. Ed. 42 4133
[6]	Eisenberg D, Shenhar R, Rabinovitz M 2010 Chem. Soc. Rev. 39 2879
[7]	Marsden J A, Miller J J, Shirtcliff L D, Haley M M 2005 J. Am. Chem. Soc. 127 2464
[8]	Zhao T, Liu Z, Song Y, Xu W, Zhang D, Zhu D 2006 J. Org. Chem. 71 7422
[9]	Xu H L, Zhong R L, Yan L K, Su Z M 2012 J. Phys. Org. Chem. 25 176
[10]	Jasti R, Bertozzi C R 2010 Chem. Phys. Lett. 494 1
[11]	Bunz U H F, Menning S, Martin N 2012 Angew. Chem. Int. Ed. 51 7094
[12]	Dai H J 2002 Acc. Chem. Res. 35 1035
[13]	Chopra N G, Luyken R J, Cherrey K, Crespi V H, Cohen M L, Louie S G, Zettl A 1995 Science 269 966
[14]	Golberg D, Bando Y, Eremets M, Takemura K, Kurashima K, Yusa H 1996 Appl. Phys. Lett. 69 2045
[15]	Han W Q, Bando Y, Kurashima K, Sato T 1998 Appl. Phys. Lett. 73 3085
[16]	Golberg D, Bando Y, Han W, Kurashima K, Sato T 1999 Chem. Phys. Lett. 308 337
[17]	Golberg D, Bando Y, Kurashima K, Sato T 2000 Chem. Phys. Lett. 323 185
[18]	Ma R, Bando Y, Sato T 2001 Chem. Phys. Lett. 337 61
[19]	Loh K P, Yang S W, Soon J M, Zhang H, Wu P 2003 J. Phys. Chem. A 107 5555
[20]	Jia J F, Wu H S 2006 Acta Phys. Chim. Sin. 22 1520 (in Chinese) [贾建峰, 武海顺 2006 物理化学学报 22 1520]
[21]	Sun W G, Liu X Y, Wang C Y, Tang Y J, Wu W D, Zhang H Q, Liu M, Yuan L, Xu J J 2009 Acta Phys. Sin. 58 1126 (in Chinese) [孙卫国, 刘秀英, 王朝阳, 唐永建, 吴卫东, 张厚琼, 刘淼, 袁磊, 徐嘉靖 2009 物理学报 58 1131]
[22]	Jia J F, Wu H S, Jiao H J 2004 Acta Chim. Sin. 62 1385 (in Chinese) [贾建峰, 武海顺, 焦海军 2004 化学学报 62 1385]
[23]	Gleiter R, Esser B, Kornmayer S C 2009 Acc. Chem. Res. 42 1108
[24]	Jasti R, Bhattacharjee J, Neaton J B, Bertozzi C R 2008 J. Am. Chem. Soc. 130 17646
[25]	Steinberg B D, Scott L T 2009 Angew. Chem. Int. Ed. 48 5400
[26]	Takaba H, Omachi H, Yamamoto Y, Bouffard J, Itami K 2009 Angew. Chem. Int. Ed. 48 6112
[27]	Omachi H, Matsuura S, Segawa Y, Itami K 2010 Angew. Chem. Int. Ed. 49 10202
[28]	Yamago S, Watanabe Y, Iwamoto T 2010 Angew. Chem. Int. Ed. 49 757
[29]	Sisto T J, Golder M R, Hirst E S, Jasti R 2011 J. Am. Chem. Soc. 133 15800
[30]	Ishii Y, Nakanishi Y, Omachi H, Matsuura S, Matsui K, Shinohara H, Segawa Y, Itami K 2012 Chem. Sci. 3 2340
[31]	Xia J, Jasti R 2012 Angew. Chem. Int. Ed. 51 2474
[32]	Segawa Y, Miyamoto S, Omachi H, Matsuura S, Šenel P, Sasamori T, Tokitoh N, Itami K 2011 Angew. Chem. Int. Ed. 50 3244
[33]	Jasti R, Sisto T 2012 Synlett. 23 483
[34]	Chen Z, Jiang D E, Lu X, Bettinger H F, Dai S, Schleyer P V, Houk K N 2007 Org. Lett. 9 5449
[35]	Choi H S, Kim K S 1999 Angew. Chem. Int. Ed. 38 2256
[36]	Chen Y K, Liu L V, Tian W Q, Wang Y A 2011 J. Phys. Chem. C 115 9306
[37]	Wang X, Liew K M 2012 J. Phys. Chem. C 116 1702
[38]	Wang C, Wang L G, Zhang H Y, Terence K S W 2010 Acta Phys. Sin. 59 536 (in Chinese) [王畅, 王利光, 张鸿宇, Terence K S W 2010 物理学报 59 536]
[39]	Yang C, Zhang B X, Feng Y F, Yu Y 2009 Acta Phys. Sin. 58 4066 (in Chinese) [杨春, 张变霞, 冯玉芳, 余毅 2009 物理学报 58 4066]
[40]	Baibarac M, Lira Cantú M, Oró Solé J, Casañ Pastor N, Gomez Romero P 2006 Small 2 1075
[41]	Liu Y Q 2010 Organic Nano and Molecular Devices (Beijing:Science Publishing House) p101 (in Chinese) [刘云圻2010 有机纳米与分子器件(北京:科学出版社) 第101页]
[42]	Schleyer P V, Maerker C, Dransfeld A, Jiao H J, Hommes N 1996 J. Am. Chem. Soc. 118 6317
[43]	Martin R L 2003 J. Chem. Phys. 118 4775
[44]	Tretiak S, Mukamel S 2002 Chem. Rev. 102 3171
[45]	Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, Nakatsuji H, Caricato M, Li X, Hratchian H P, Izmaylov A F, Bloino J, Zheng G, Sonnenberg J L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr J A, Peralta J E, Ogliaro F, Bearpark M, Heyd J J, Brothers E, Kudin K N, Staroverov V N, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J C, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam J M, Klene M, Knox J E, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Martin R L, Morokuma K, Zakrzewski V G, Voth G A, Salvador P, Dannenberg J J, Dapprich S, Daniels A D, Farkas O, Foresman J B, Ortiz J V, Cioslowski J, Fox D J 2009 Gaussian 09 (Revision A.02 Gaussian, Inc. Wallingford CT)
[46]	Zhao Y, Truhlar D G 2008 Acc. Chem. Res. 41 157
[47]	Scholes G D, Tretiak S, McDonald T J, Metzger W K, Engtrakul C, Rumbles G, Heben M J 2007 J. Phys. Chem. C 111 11139
[48]	Wong B M 2009 J. Phys. Chem. C 113 21921

Cited By

[1]	Iijima S 1991 Nature 354 56
[2]	Prasek J, Drbohlavova J, Chomoucka J, Hubalek J, Jasek O, Adam V, Kizek R 2011 J. Mater. Chem. 21 15872
[3]	Omachi H, Segawa Y, Itami K 2012 Acc. Chem. Res. 45 1378
[4]	Kawase T, Kurata H 2006 Chem. Rev. 106 5250
[5]	Scott L T 2003 Angew. Chem. Int. Ed. 42 4133
[6]	Eisenberg D, Shenhar R, Rabinovitz M 2010 Chem. Soc. Rev. 39 2879
[7]	Marsden J A, Miller J J, Shirtcliff L D, Haley M M 2005 J. Am. Chem. Soc. 127 2464
[8]	Zhao T, Liu Z, Song Y, Xu W, Zhang D, Zhu D 2006 J. Org. Chem. 71 7422
[9]	Xu H L, Zhong R L, Yan L K, Su Z M 2012 J. Phys. Org. Chem. 25 176
[10]	Jasti R, Bertozzi C R 2010 Chem. Phys. Lett. 494 1
[11]	Bunz U H F, Menning S, Martin N 2012 Angew. Chem. Int. Ed. 51 7094
[12]	Dai H J 2002 Acc. Chem. Res. 35 1035
[13]	Chopra N G, Luyken R J, Cherrey K, Crespi V H, Cohen M L, Louie S G, Zettl A 1995 Science 269 966
[14]	Golberg D, Bando Y, Eremets M, Takemura K, Kurashima K, Yusa H 1996 Appl. Phys. Lett. 69 2045
[15]	Han W Q, Bando Y, Kurashima K, Sato T 1998 Appl. Phys. Lett. 73 3085
[16]	Golberg D, Bando Y, Han W, Kurashima K, Sato T 1999 Chem. Phys. Lett. 308 337
[17]	Golberg D, Bando Y, Kurashima K, Sato T 2000 Chem. Phys. Lett. 323 185
[18]	Ma R, Bando Y, Sato T 2001 Chem. Phys. Lett. 337 61
[19]	Loh K P, Yang S W, Soon J M, Zhang H, Wu P 2003 J. Phys. Chem. A 107 5555
[20]	Jia J F, Wu H S 2006 Acta Phys. Chim. Sin. 22 1520 (in Chinese) [贾建峰, 武海顺 2006 物理化学学报 22 1520]
[21]	Sun W G, Liu X Y, Wang C Y, Tang Y J, Wu W D, Zhang H Q, Liu M, Yuan L, Xu J J 2009 Acta Phys. Sin. 58 1126 (in Chinese) [孙卫国, 刘秀英, 王朝阳, 唐永建, 吴卫东, 张厚琼, 刘淼, 袁磊, 徐嘉靖 2009 物理学报 58 1131]
[22]	Jia J F, Wu H S, Jiao H J 2004 Acta Chim. Sin. 62 1385 (in Chinese) [贾建峰, 武海顺, 焦海军 2004 化学学报 62 1385]
[23]	Gleiter R, Esser B, Kornmayer S C 2009 Acc. Chem. Res. 42 1108
[24]	Jasti R, Bhattacharjee J, Neaton J B, Bertozzi C R 2008 J. Am. Chem. Soc. 130 17646
[25]	Steinberg B D, Scott L T 2009 Angew. Chem. Int. Ed. 48 5400
[26]	Takaba H, Omachi H, Yamamoto Y, Bouffard J, Itami K 2009 Angew. Chem. Int. Ed. 48 6112
[27]	Omachi H, Matsuura S, Segawa Y, Itami K 2010 Angew. Chem. Int. Ed. 49 10202
[28]	Yamago S, Watanabe Y, Iwamoto T 2010 Angew. Chem. Int. Ed. 49 757
[29]	Sisto T J, Golder M R, Hirst E S, Jasti R 2011 J. Am. Chem. Soc. 133 15800
[30]	Ishii Y, Nakanishi Y, Omachi H, Matsuura S, Matsui K, Shinohara H, Segawa Y, Itami K 2012 Chem. Sci. 3 2340
[31]	Xia J, Jasti R 2012 Angew. Chem. Int. Ed. 51 2474
[32]	Segawa Y, Miyamoto S, Omachi H, Matsuura S, Šenel P, Sasamori T, Tokitoh N, Itami K 2011 Angew. Chem. Int. Ed. 50 3244
[33]	Jasti R, Sisto T 2012 Synlett. 23 483
[34]	Chen Z, Jiang D E, Lu X, Bettinger H F, Dai S, Schleyer P V, Houk K N 2007 Org. Lett. 9 5449
[35]	Choi H S, Kim K S 1999 Angew. Chem. Int. Ed. 38 2256
[36]	Chen Y K, Liu L V, Tian W Q, Wang Y A 2011 J. Phys. Chem. C 115 9306
[37]	Wang X, Liew K M 2012 J. Phys. Chem. C 116 1702
[38]	Wang C, Wang L G, Zhang H Y, Terence K S W 2010 Acta Phys. Sin. 59 536 (in Chinese) [王畅, 王利光, 张鸿宇, Terence K S W 2010 物理学报 59 536]
[39]	Yang C, Zhang B X, Feng Y F, Yu Y 2009 Acta Phys. Sin. 58 4066 (in Chinese) [杨春, 张变霞, 冯玉芳, 余毅 2009 物理学报 58 4066]
[40]	Baibarac M, Lira Cantú M, Oró Solé J, Casañ Pastor N, Gomez Romero P 2006 Small 2 1075
[41]	Liu Y Q 2010 Organic Nano and Molecular Devices (Beijing:Science Publishing House) p101 (in Chinese) [刘云圻2010 有机纳米与分子器件(北京:科学出版社) 第101页]
[42]	Schleyer P V, Maerker C, Dransfeld A, Jiao H J, Hommes N 1996 J. Am. Chem. Soc. 118 6317
[43]	Martin R L 2003 J. Chem. Phys. 118 4775
[44]	Tretiak S, Mukamel S 2002 Chem. Rev. 102 3171
[45]	Frisch M J, Trucks G W, Schlegel H B, Scuseria G E, Robb M A, Cheeseman J R, Scalmani G, Barone V, Mennucci B, Petersson G A, Nakatsuji H, Caricato M, Li X, Hratchian H P, Izmaylov A F, Bloino J, Zheng G, Sonnenberg J L, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery Jr J A, Peralta J E, Ogliaro F, Bearpark M, Heyd J J, Brothers E, Kudin K N, Staroverov V N, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant J C, Iyengar S S, Tomasi J, Cossi M, Rega N, Millam J M, Klene M, Knox J E, Cross J B, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann R E, Yazyev O, Austin A J, Cammi R, Pomelli C, Ochterski J W, Martin R L, Morokuma K, Zakrzewski V G, Voth G A, Salvador P, Dannenberg J J, Dapprich S, Daniels A D, Farkas O, Foresman J B, Ortiz J V, Cioslowski J, Fox D J 2009 Gaussian 09 (Revision A.02 Gaussian, Inc. Wallingford CT)
[46]	Zhao Y, Truhlar D G 2008 Acc. Chem. Res. 41 157
[47]	Scholes G D, Tretiak S, McDonald T J, Metzger W K, Engtrakul C, Rumbles G, Heben M J 2007 J. Phys. Chem. C 111 11139
[48]	Wong B M 2009 J. Phys. Chem. C 113 21921

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Vol. 62, Issue 8 - 2013-04-20

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