Paper
PCCP
15 K. Nasu, T. Nakagawa, H. Nomura, C.-J. Lin, C.-H. Cheng,
M.-R. Tseng, T. Yasuda and C. Adachi, Chem. Commun.,
2013, 49, 10385–10387.
16 S. S. Babu, M. J. Hollamby, J. Aimi, H. Ozawa, A. Saeki,
S. Seki, K. Kobayashi, K. Hagiwara, M. Yoshizawa,
H. Mohwald and T. Nakanishi, Nat. Commun., 2013, 4,
1969.
17 S. H. Lee, J. R. Lott, Y. C. Simon and Ch. Weder, J. Mater.
Chem. C, 2013, 1, 5142.
18 P. Duan, N. Yanai and N. Kimizuka, J. Am. Chem. Soc., 2013,
135, 19056–19059.
quenching as compared to the substitution by the 2-phenyl
group and also with respect to the unsubstituted DPA. The
influence of the alkyl groups attached at the para position of
9,10-phenyls on the optical properties was found to be insigni-
ficant, whereas they strongly affected film forming and charge
transport properties. It is worth noting that the non-symmetric
DPA derivatives expressed very high hole drift mobilities of up
to 4.6 Â 10À3 cm2 VÀ1 sÀ1 for 2-phenyl-substituted compounds
and up to almost 1 Â 10À2 cm2 VÀ1 sÀ1 for 2-pentyl-substituted
analogues at an electric field of 1 MV cmÀ1
.
Further optimization of the DPA at the 2nd position by
introducing non-conjugated and more branched or bulky sub-
stituents should enable to achieve an even higher glass transi-
tion temperature and carrier drift mobility while preserving the
high fluorescence efficiency.
19 I. Cho, S. H. Kim, J. H. Kim, S. Park and S. Y. Park, J. Mater.
Chem., 2012, 22, 123–129.
20 B. Valeur, Molecular Fluorescence: Principles and Applications,
Wiley-VCH, Weinheim, New York, 2002.
21 N. Nijegorodov, P. V. C. Luhanga, J. S. Nkoma and D. P.
Winkoun, Spectrochim. Acta, Part A, 2006, 64, 1–5.
22 J. V. Morris, M. A. Mahaney and J. R. Huber, J. Phys. Chem.,
1976, 80, 969–974.
23 C. Adachi, T. Tsutsui and S. Saito, Appl. Phys. Lett., 1990,
56, 799.
24 J.-K. Bin and J.-I. Hong, Org. Electron., 2011, 12, 802–808.
25 W. J. Jo, K.-H. Kim, H. C. No, D.-Y. Shin, S.-J. Oh, J.-H. Son,
Y.-H. Kim, Y.-K. Cho, Q.-H. Zhao, K.-H. Lee, H.-Y. Oh and
S.-K. Kwon, Synth. Met., 2009, 159, 1359–1364.
26 S. C. Tse, S. K. So, M. Y. Yeung, C. F. Lo, S. W. Wen and
C. H. Chen, Chem. Phys. Lett., 2006, 422, 354–357.
27 M.-H. Ho, Y.-S. Wu, S.-W. Wen, M.-T. Lee, T.-M. Chen,
C. H. Chen, K.-C. Kwok, S.-K. So, K.-T. Yeung, Y.-K. Cheng
and Z.-Q. Gao, Appl. Phys. Lett., 2006, 89, 252903.
28 M.-H. Ho, B. Balaganesan and C. H. F. Chen, Isr. J. Chem.,
2012, 52, 484–495.
Acknowledgements
The research was funded by a grant (No. 31V-28) from the
Science, Innovation and Technology Agency. The public access
supercomputer from the High Performance Computing Center
(HPCC) of the Lithuanian National Center of Physical and
Technology Sciences (NCPTS) at Physics Faculty of Vilnius
˙
University (HPC Sauletekis) was used for DFT calculations.
References
1 H. D. Becker, Chem. Rev., 1993, 93, 145–172.
2 M. Agbandje, T. C. Jenkins, R. McKenna, A. P. Reszka and
S. Neidle, J. Med. Chem., 1992, 35, 1418–1429.
3 S. Miyata, Organic Electroluminescent Materials and Devices,
CRC Press, Florida, 1997.
4 Y. Inoue, S. Tokito, K. Ito and T. Suzuki, J. Appl. Phys., 2004,
95, 5795–5799.
5 H. Meng, F. P. Sun, M. B. Goldfinger, G. D. Jaycox, Z. G. Li,
W. J. Marshall and G. S. Blackman, J. Am. Chem. Soc., 2005,
127, 2406–2407.
29 Y.-J. Pu, A. Kamiya, K. Nakayama and J. Kido, Org. Electron.,
2010, 11, 479–485.
30 Y. Sun, L. Duan, D. Zhang, J. Qiao, G. Dong, L. Wang and
Y. Qiu, Adv. Funct. Mater., 2011, 21, 1881–1886.
31 J. C. de Mello, H. F. Wittmann and R. H. Friend, Adv. Mater.,
1997, 9, 230–232.
32 P. M. Borsenberger, Organic Photoreceptors for Xerography,
Marcel Dekker, New York, 1998.
33 E. Montrimas, V. Gaidelis and A. Pazera, Lith. J. Phys, 1966,
6, 569–576.
6 D. S. Chung, J. W. Park, J.-H. Park, D. Moon, G. H. Kim,
H.-S. Lee, D. H. Lee, H.-K. Shim, S.-K. Kwon and C. E. Park,
J. Mater. Chem., 2010, 20, 524–530.
7 L. Valentini, D. Bagnis, A. Marrocchi, M. Seri, A. Taticchi
and J. M. Kenny, Chem. Mater., 2008, 20, 32–34.
34 S. M. Vaezi-Nejad, Int. J. Electron., 1987, 62, 361–384.
ˇ
8 C. Teng, X. Yang, C. Yang, S. Li, M. Cheng, A. Hagfeldt and 35 V. Sivamurugan, R. Lygaitis, J. V. Graˇzulevicius, V. Gaidelis,
L. Sun, J. Phys. Chem. C, 2010, 114, 9101–9110.
9 J. Shi and C. W. Tang, Appl. Phys. Lett., 2002, 80, 3201.
V. Jankauskas and S. Valiyaveettil, J. Mater. Chem., 2009,
19, 4268.
10 R. Kim, S. Lee, K.-H. Kim, Y.-J. Lee, S.-K. Kwon, J.-J. Kim and 36 M. Kirkus, R. Lygaitis, M.-H. Tsai, J. V. Grazulevicius and
Y.-H. Kim, Chem. Commun., 2013, 49, 4664.
C.-C. Wu, Synth. Met., 2008, 158, 226–232.
11 S.-K. Kim, B. Yang, Y. Ma, J.-H. Lee and J.-W. Park, J. Mater. 37 M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria and
Chem., 2008, 18, 3376.
M. A. Robb, et al., Gaussian 09, Gaussian Inc., Wallingford,
12 D. Y. Kondakov, J. Appl. Phys., 2007, 102, 114504.
CT, 2013.
13 H. Fukagawa, T. Shimizu, N. Ohbe, S. Tokito, K. Tokumaru 38 A. V. Kukhta, I. N. Kukhta, N. A. Kukhta, O. L. Neyra and
and H. Fujikake, Org. Electron., 2012, 13, 1197–1203. E. Meza, J. Phys. B: At., Mol. Opt. Phys., 2008, 41, 205701.
14 C.-J. Chiang, A. Kimyonok, M. K. Etherington, G. C. Griffiths, 39 T. Serevicius, P. Adomenas, O. Adomeniene, R. Rimkus,
ˇ
˙
˙
˙
ˇ˙
V. Jankus, F. Turksoy and A. P. Monkman, Adv. Funct. Mater.,
2013, 23, 739–746.
V. Jankauskas, A. Gruodis, K. Kazlauskas and S. Jursenas,
Dyes Pigm., 2013, 98, 304–315.
7100 | Phys. Chem. Chem. Phys., 2014, 16, 7089--7101
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