Abstract
Exploring and synthesizing new simple n-channel organic semiconductor materials with large electron mobility and high air stability have remained a major challenge and hot issue in the field of organic electronics. In the current work, the electron transport properties of four novel nitrogen-rich pentacene derivatives (PBD1, PBD2, PBD3, and PBD4) with two cyano groups as potential n-channel OFET materials have been investigated at the molecular and crystal levels by means of density functional theory (DFT) calculations coupled with the prediction of crystal structures and the incoherent charge-hopping model. Calculations reveal that the studied compounds, which possess low-lying frontier molecular energy levels, large ionization potentials and electron affinities, are very stable exposed to air. Based on predicted crystal structures, the average electron mobility at room temperature (T = 300 K) for PBD1, PBD2, PBD3, and PBD4 is predicted to be as high as 0.950, 0.558, 0.518, and 1.052 cm2·V−1·s−1, which indicate that these four compounds are more than likely to be promising candidates as n-type OFET materials under favorable device conditions. However, this claim needs experimental verification. In addition, the angular-dependent simulation for electron mobility shows that the electron transport is remarkably anisotropic in these molecular crystals and the maximum μ e appears along the crystal axis direction since molecules along this direction exhibit the close face-to-face stacking arrangement with short interplanar distances (~3.6-4.0 Å), which induces large electronic couplings.
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Wang CL, Dong HL, Hu WP, Liu YQ, Zhu DB (2012) Chem Rev 112:2208–2267
Menard E, Meitl MA, Sun YG, Park J-U, Shir DJ-L, Nam Y-S, Jeon S, Rogers JA (2007) Chem Rev 107:1117–1160
Cheng Y-J, Yang S-H, Hsu C-S (2009) Chem Rev 109:5868–5923
Jurchescu OD, Baas J, Palstra TTM (2004) Appl Phys Lett 84:3061–3063
Podzorov V, Menard E, Borissov A, Kiryukhin V, Rogers JA, Gershenson ME (2004) Phys Rev Lett 93:086602
Zhao Y, Di C-A, Gao XK, Hu YB, Guo YL, Zhang L, Liu YQ, Wang JZ, Hu WP, Zhu DB (2011) Adv Mater 23:2448–2453
Street RA (2009) Adv Mater 21:2007–2022
Kuo M-Y, Chen H-Y, Chao I (2007) Chem Eur J 13:4750–4758
Liu C-C, Mao S-W, Kuo M-Y (2010) J Phys Chem C 114:22316–22321
Sun H, Putta A, Billion M (2012) J Phys Chem A 116:8015–8022
Chai S, Wen S-H, Huang J-D, Han K-L (2011) J Comput Chem 32:3218–3225
Hutchison GR, Ratner MA, Marks TJ (2005) J Am Chem Soc 127:2339–2350
Chen X-K, Guo J-F, Zou L-Y, Ren A-M (2011) J Phys Chem C 115:21416–21428
Gao BX, Wang M, Cheng YX, Wang LX, Jing XB, Wang FS (2008) J Am Chem Soc 130:8297–8306
Wang HF, Wen YG, Yang XD, Wang Y, Zhou WY, Zhang SM, Zhan XW, Liu YQ, Shuai ZG, Zhu DB (2009) ACS Appl Mater Interf 1:1122–1129
Winkler M, Houk KN (2007) J Am Chem Soc 129:1805–1815
Hanwell MD, Madison TA, Hutchison GR (2010) J Phys Chem C 114:20417–20423
Marcus RA (1956) J Chem Phys 24:966–978
Hush NS (1958) J Chem Phys 28:962–972
Malagoli M, Brédas JL (2000) Chem Phys Lett 327:13–17
Lemaur V, da Silva Filho DA, Coropceanu V, Lehmann M, Geerts Y, Piris J, Debije MG, van de Craats AM, Senthilkumar K, Siebbeles LDA, Warman JM, Brédas J-L, Cornil J (2004) J Am Chem Soc 126:3271–3279
Sanchez-Carrera RS, Coropceanu V, da Silva Filho DA, Friedlein R, Osikowicz W, Murdey R, Suess C, Salaneck WR, Brédas J-L (2006) J Phys Chem B 110:18904–18911
Brédas J-L, Beljonne D, Coropceanu V, Cornil J (2004) Chem Rev 104:4971–5003
Chen H-Y, Chao I (2005) Chem Phys Lett 401:539–545
Barbara PF, Meyer TJ, Ratner MA (1996) J Phys Chem 100:13148–13168
Troisi A, Orlandi G (2002) J Phys Chem B 106:2093–2101
Newton MD (1991) Chem Rev 91:767–792
Cave RJ, Newton MD (1997) J Chem Phys 106:9213–9226
Valeev EF, Coropceanu V, da Silva Filho DA, Salman S, Brédas J-L (2006) J Am Chem Soc 128:9882–9886
Nan GJ, Wang LJ, Yang XD, Shuai ZG, Zhao Y (2009) J Chem Phys 130:024704
Wang LJ, Nan GJ, Yang XD, Peng Q, Li QK, Shuai ZG (2010) Chem Soc Rev 39:423–434
Senthilkumar K, Grozema FC, Guerra CF, Bickelhaupt FM, Lewis FD, Berlin YA, Ratner MA, Siebbeles LDA (2005) J Am Chem Soc 127:14894–14903
Zhang WW, Zhu WJ, Liang WZ, Zhao Y, Nelsen SF (2008) J Phys Chem B 112:11079–11086
Lowdin P-O (1950) J Chem Phys 18:365–375
Gao HZ, Qin CS, Zhang HY, Wu SX, Su ZM, Wang Y (2008) J Phys Chem A 112:9097–9103
Yin SW, Yi YP, Li QX, Yu G, Liu YQ, Shuai ZG (2006) J Phys Chem A 110:7138–7143
Song YB, Di CA, Yang XD, Li SP, Xu W, Liu YQ, Yang LM, Shuai ZG, Zhang DQ, Zhu DB (2006) J Am Chem Soc 128:15940–15941
Einstein A (1905) Ann Phys 17:549–560
van Smoluchowski M (1906) Ann Phys 21:756–780
Gao HZ (2010) Theor Chem Acc 127:759–763
Wen S-H, Li A, Song J-L, Deng W-Q, Han K-L, Goddard WA III (2009) J Phys Chem B 113:8813–8819
Huang J-D, Wen S-H, Deng W-Q, Han K-L (2011) J Phys Chem B 115:2140–2147
Yin SW, Li LL, Yang YM, Reimers JR (2012) J Phys Chem C 116:14826–14836
Pasveer WF, Cottaar J, Tanase C, Coehoorn R, Bobbert PA, Blom PWM, de Leeuw DM, Michels MAJ (2005) Phys Rev Lett 94:206601
Chatten AJ, Tuladhar SM, Choulis SA, Bradley DDC, Nelson J (2005) J Mater Sci 40:1393–1398
Yu ZG, Smith DL, Saxena A, Martin RL, Bishop AR (2001) Phys Rev B 63:085202
Yin SW, Lv YF (2008) Org Electron 9:852–858
Delgado MCR, Kim E-G, da Silva Filho DA, Brédas J-L (2010) J Am Chem Soc 132:3375–3387
Chen X-K, Zou L-Y, Huang S, Min C-G, Ren A-M, Feng J-K, Sun C-C (2011) Org Electron 12:1198–1210
Hutchison GR, Ratner MA, Marks TJ (2005) J Am Chem Soc 127:16866–16881
Kera S, Hosoumi S, Sato K, Fukagawa H, Nagamatsu S, Sakamoto Y, Suzuki T, Huang H, Chen W, Wee ATS, Coropceanu V, Ueno N (2013) J Phys Chem C 117:22428–22437
Gruhn NE, da Silva Filho DA, Bill TG, Malagoli M, Coropceanu V, Kahn A, Brédas J-L (2002) J Am Chem Soc 124:7918–7919
Becke AD (1993) J Chem Phys 98:5648–5652
Lee C, Yang W, Parr RG (1988) Phys Rev B 37:785–789
Clark T, Chandrasekhar J, Spitznagel GW, Schleyer PVR (1983) J Comput Chem 4:294–301
Weber P, Reimers JR (1999) J Phys Chem A 103:9830–9841
Cai Z-L, Reimers JR (2000) J Phys Chem A 104:8389–8408
Brovchenko IV (1997) Chem Phys Lett 278:355–359
McMahon DP, Troisi A (2010) J Phys Chem Lett 1:941–946
Zhan C-G, Nichols JA, Dixon DA (2003) J Phys Chem A 107:4184–4195
Rienstra-Kiracofe JC, Tschumper GS, Schaefer HF, Nandi S, Ellison GB (2002) Chem Rev 102:231–282
Muscat J, Wander A, Harrison NM (2001) Chem Phys Lett 342:397–401
Huang JS, Kertesz M (2004) Chem Phys Lett 390:110–115
Yang XD, Wang LJ, Wang CL, Long W, Shuai ZG (2008) Chem Mater 20:3205–3211
Wang CL, Wang FH, Yang XD, Li QK, Shuai ZG (2008) Org Electron 9:635–640
Frisch MJ, Trucks GW, Schlegel HB, Scuseria GE, Robb MA, Cheeseman JR, Scalmani G, Barone V, Mennucci B, Petersson GA, Nakatsuji H, Caricato M, Li X, Hratchian HP, Izmaylov AF, Bloino J, Zheng G, Sonnenberg JL, Hada M, Ehara M, Toyota K, Fukuda R, Hasegawa J, Ishida M, Nakajima T, Honda Y, Kitao O, Nakai H, Vreven T, Montgomery JJA, Peralta JE, Ogliaro F, Bearpark M, Heyd JJ, Brothers E, Kudin KN, Staroverov VN, Kobayashi R, Normand J, Raghavachari K, Rendell A, Burant JC, Iyengar SS, Tomasi J, Cossi M, Rega N, Millam JM, Klene M, Knox JE, Cross JB, Bakken V, Adamo C, Jaramillo J, Gomperts R, Stratmann RE, Yazyev O, Austin AJ, Cammi R, Pomelli C, Ochterski JW, Martin RL, Morokuma K, Zakrzewski VG, Voth GA, Salvador P, Dannenberg JJ, Dapprich S, Daniels AD, Farkas O, Foresman JB, Ortiz JV, Cioslowski J, Fox DJ (2010) Gaussian 09, in: Revision C.03. Gaussian Inc, Wallingford
van Eijck BP, Kroon J (1999) J Comput Chem 20:799–812
Day GM, Chisholm J, Shan N, Sam Motherwell WD, Jones W (2004) Cryst Growth Des 4:1327–1340
Panina N, Leusen FJJ, Janssen FFBJ, Verwer P, Meekes H, Vlieg E, Deroover G (2007) J Appl Cryst 40:105–114
Gdanitz RJ (1992) Chem Phys Lett 190:391–396
Chang Y-F, Lu Z-Y, An L-J, Zhang J-P (2012) J Phys Chem C 116:1195–1199
Lin LL, Geng H, Shuai ZG, Luo Y (2012) Org Electron 13:2763–2772
Köhler A, Khan AL, Wilson JS, Dosche C, Al-Suti MK, Shah HH, Khan MS (2012) J Chem Phys 136:094905
Lee JY, Lee SJ, Kim KS (1997) J Chem Phys 107:4112–4117
Kwiatkowski JJ, Nelson J, Li H, Bredas JL, Wenzel W, Lennartz C (2008) Phys Chem Chem Phys 10:1852–1858
Usta H, Risko C, Wang ZM, Huang H, Deliomeroglu MK, Zhukhovitskiy A, Facchetti A, Marks TJ (2009) J Am Chem Soc 131:5586–5608
Chang Y-C, Kuo M-Y, Chen C-P, Lu H-F, Chao I (2010) J Phys Chem C 114:11595–11601
Newman CR, Frisbie CD, da Silva Filho DA, Brédas J-L, Ewbank PC, Mann KR (2004) Chem Mater 16:4436–4451
Coropceanu V, Cornil J, da Silva Filho DA, Olivier Y, Silbey R, Brédas J-L (2007) Chem Rev 107:926–952
Oehzelt M, Aichholzer A, Resel R, Heimel G, Venuti E, Della Valle RG (2006) Phys Rev B 74:104103
Brédas J-L, Calbert JP, da Silva Filho DA, Cornil J (2002) Proc Natl Acad Sci U S A 99:5804–5809
Usta H, Facchetti A, Marks TJ (2011) Acc Chem Res 44:501–510
Usta H, Facchetti A, Marks TJ (2008) Org Lett 10:1385–1388
Acknowledgments
This work is supported by the National Nature Science Foundation of China (21173139, 21173138), the Fundamental Research Funds for the Central Universities (GK201303004), the Shaanxi Innovative Team of Key Science and Technology (2013KCT-17), and the Innovation Funds of Graduate Programs of the Shaanxi Normal University (2013CXB023).
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Zhao, C., Ge, H., Yin, S. et al. Theoretical investigation on the crystal structures and electron transport properties of several nitrogen-rich pentacene derivatives. J Mol Model 20, 2158 (2014). https://doi.org/10.1007/s00894-014-2158-z
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DOI: https://doi.org/10.1007/s00894-014-2158-z