Fig. 3 Normalized solid-state luminescence of (a) CDPA, 1–4 and (b) solvent dependent luminescence of 3 (excitation l = 370 nm).
M = 971.17, orthorhombic, Pbcn, a = 32.166(2), b = 9.900(7), c =
˚
˚
1
6.407(1) A, V = 5224.4(6) A, Z = 4, T = 150 K, 53 187 reflections
measured, 4686 unique (Rint = 0.0287), final R values: 0.0490, wR:
.1398; 4 (CCDC 737401): C22 , C 10NO, M = 427.49,
0
H
15
N
2
O
2
4
H
ꢀ
˚
triclinic, P1,a = 11.231(1), b = 16.368(1), c = 26.031(2) A, a =
3
˚
9
9.435(1), b = 102.219 (1), g = 99.471(2), V = 4514.0(6) A , Z = 8,
T = 150 K, 49 086 reflections measured, 15 976 unique (Rint = 0.0505),
final R values: 0.0580, wR: 0.1282.
1
2
(a) H. Yersin, Highly Efficient OLEDs with Phosphorescent Materials,
Wiley-VCH, Weinheim, 2008; (b) K. Mullen and U. Scherf, Organic
Light-Emitting Devices, Synthesis Properties and Applications,
Wiley-VCH, Weinheim, 2006.
(a) I. D. W. Samuel and G. A. Turnbull, Chem. Rev., 2007, 107,
¨
1
272; (b) U. Scherf, S. Riechel, U. Lemmer and R. F. Mahrt, Curr.
Opin. Solid State Mater. Sci., 2001, 5, 143; (c) M. D. McGehee and
A. J. Heeger, Adv. Mater., 2000, 12, 1655; (d) G. Kranzelbinder
and G. Leising, Rep. Prog. Phys., 2000, 63, 729; (e) N. Tessler,
Adv. Mater., 1999, 11, 363.
3
4
(a) S. W. Thomas Iii, G. D. Joly and T. M. Swager, Chem. Rev., 2007,
107, 1339; (b) L. Basabe-Desmonts, D. N. Reinhoudt and M. Crego-
Calama, Chem. Soc. Rev., 2007, 36, 993; (c) O. S. Wolfbeis, J. Mater.
Chem., 2005, 15, 2657; (d) A. P. de Silva, H. Q. N. Gunaratne,
T. Gunnlaugsson, A. J. M. Huxley, C. P. McCoy, J. T. Rademacher
and T. E. Rice, Chem. Rev., 1997, 97, 1515.
Fig. 4 Switching of solid-state CDPA luminescence. Arrow indicates
the time required for the conversion (excitation l = 370 nm).
leads to the gradual blue shift of CDPA solid-state
3
luminescence from 587 nm to 494 nm. 3 gives a CH CN
W. Frank, A. Shahadat, T. Christoph and D. Tony, Chem.–Eur. J.,
2
selective supramolecular luminescent host system. Tuning
and indeed switching of the luminescence is demonstrated by
exposing powdered CDPA to amine vapor (pyrrolidine,
morpholine) and HCl solution. Developments of chiral supra-
molecular luminescent host systems based on CDPA are
underway.
002, 8, 4742.
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1999, 38, 2722; (b) R. A. van Delden, N. P. M. Huck, J. J. Piet,
J. M. Warman, S. C. J. Meskers, H. P. J. M. Dekkers and
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(c) S. M. Draper, D. Gregg and R. Madathil, J. Am. Chem. Soc.,
2002, 124, 3486.
6
7
G. Nishimura, H. Maehara, Y. Shiraishi and T. Hirai, Chem.–Eur.
J., 2008, 14, 259.
(a) H. Liu, Y. Hung, C. Chou and C. Su, Chem. Commun., 2007,
This material is based upon works supported by EU FP6
[
[
MKTD-CT-2004-014472] and Science Foundation Ireland
05PICAI819].
4
95; (b) A. Patra and T. P. Radhakrishnan, Chem.–Eur. J., 2009,
5, 2792.
1
8
(a) Q. Liu, M. S. Mudadu, R. Thummel, Y. Tao and S. Wang, Adv.
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Notes and references
z Crystal data: CDPA (CCDC: 737400): C22
16 2 2
H N O , M = 340.37,
˚
monoclinic, P2
1
1
/n, a = 13.568(1), b = 9.459(1), c = 13.642(1) A, b =
9 R. Davis, N. P. Rath and S. Das, Chem. Commun., 2004, 74.
10 (a) T. Mutai, H. Tomoda, T. Ohkawa, Y. Yabe and K. Araki,
Angew. Chem., Int. ed., 2008, 47, 9522; (b) T. Mutai, H. Satou and
K. Araki, Nat. Mater., 2005, 4, 685.
11 Y. Mizobe, M. Miyata, I. Hisaki, Y. Hasegawa and N. Tohnai,
Org. Lett., 2006, 8, 4295.
3
04.167(2), V = 1697.6(3) A , Z = 4, T = 150 K, 9595 reflections
˚
measured, 2985 unique (Rint = 0.0248), final R values: 0.0330, wR:
.0893; 1 (CCDC 737402): 2(C22 ), C N, M = 759.84,
0
monoclinic, P2
9
H
16
N
2
O
2
5 5
H
˚
1
/c, a = 7.877(1), b = 9.424(1), c = 26.835(3) A, b =
3
3.023(3), V = 1989.3(4) A , Z = 2, T = 150 K, 11 236 reflections
˚
measured, 3497 unique (Rint = 0.0307), final R values: 0.0553, wR:
.1404; 2 (CCDC 737399): C22 , C N, M = 411.49, mono-
12 (a) Y. Mizobe, N. Tohnai, M. Miyata and Y. Hasegawa, Chem.
Commun., 2005, 1839; (b) Y. Imai, K. Murata, K. Kawaguchi,
T. Sato, R. Kuroda and Y. Matsubara, Org. Lett., 2007, 9, 3457.
13 D. P. Hagberg, T. Marinado, K. M. Kalsson, K. Nonomura,
P. Qin, G. Boschloo, T. Brinck, A. Hadfeldt and L. Sun,
J. Org. Chem., 2007, 72, 9550.
0
clinic, P2
16
H N
O
2 2
4 9
H
˚
1
/c, a = 9.461(1), b = 25.424(2), c = 11.161(1) A, b =
3
25.704(5), V = 2180.0(3) A , Z = 4, T = 150 K, 12 692 reflections
˚
1
measured, 3855 unique (Rint = 0.0402), final R values: 0.0611, wR:
.1660; 3 (CCDC 737403): 2(C22 ), 2(C 11N), 3(C N),
0
H
16
N
2
O
2
5
H
2 3
H
7
502 | Chem. Commun., 2009, 7500–7502
This journal is ꢁc The Royal Society of Chemistry 2009