Abstract
Three symmetrical and unsymmetrical trans-dithienylethenes functionalized with pyridines and fluorenes have been synthesized by a facile one-pot procedure, and their characteristics and photochromism were investigated. Their fluorescent intensity was efficiently regulated by a photochromic switch using alternative irradiation with UV light and visible light. Moreover, by protonation and complexation, the pyridyl-substituted compounds also showed excellent photoswitching properties with distinguishable color changes. These characteristics are expected to be applicable to potential multi-addressable photoswitch and erasable optical data processing technologies.
Similar content being viewed by others
References
B. L. Feringa, Molecular Switches, Wiley-VCH, Weinheim, 2001.
M. Irie, Diarylethenes for memories and switches, Chem. Rev., 2000, 100, 1685–1716.
H. Tian, S. J. Yang, Recent progresses on diarylethene based photochromic switches, Chem. Soc. Rev., 2004, 33, 85–97
H. Tian, S. Wang, Photochromic bisthienylethene as multi-function switches, Chem. Commun., 2007, 781–792.
S. Kobatake and M. Irie, Photochromism, Annu. Rep. Prog. Chem., Sect. C, 2003, 99, 277–313.
T. J. Wigglesworth, A. J. Myles and N. R. Branda, High-content photochromic polymers based on dithienylethenes, Eur. J. Org. Chem., 2005, 1233–1238.
G. Y. Jiang, Y. L. Song, X. F. Guo, D. Q. Zhang and D. B. Zhu, Organic functional molecules towards information processing and high-density information storage, Adv. Mater., 2008, 20, 2888–2898.
V. W. W. Yam, J. K. W. Lee, C. C. Ko and N. Y. Zhu, Photochromic diarylethene-containing ionic liquids and N-heterocyclic carbenes, J. Am. Chem. Soc., 2009, 131, 912–913.
A. J. Myles, T. J. Wigglesworth and N. R. Branda, A multi-addressable photochromic 1,2-dithienylcyclopentene-phenoxy-naphthacenequin-one hybrid, Adv. Mater., 2003, 15, 745–748.
R. B. Woodward and R. H. Hoffmann, The Conservation of Orbital Symmetry, Verlag Chemie, Germany, 1970.
M. Irie and M. Mohri, Thermally irreversible photochromic systems. reversible photocyclization of diarylethene derivatives, J. Org. Chem., 1988, 53, 803–808.
M. M. Krayushkin, Synthesis of photochromic dihetarylethenes, Chem. Heterocycl. Compd., 2001, 37, 15–36.
T. Yamaguchi, K. Uchida and M. Irie, Asymmetric photocyclization of diarylethene derivatives, J. Am. Chem. Soc., 1997, 119, 6066–6071.
Y. C. Jeong, D. G. Park, I. S. Lee, S. I. Yang and K. H. Ahn, Highly fluorescent photochromic diarylethene with an excellent fatigue property, J. Mater. Chem., 2009, 19, 97–103.
L. N. Lucas, J. de Jong, J. van Esch, R. M. Kellogg, B. L. Feringa, Syntheses of dithienylcyclopentene optical molecular switches, Eur. J. Org. Chem., 2003, 155–166
L. N. Lucas, J. van Esch, R. M. Kellogg, B. L. Feringa, A new synthetic route to symmetrical photochromic diarylperfluorocyclopentenes, Tetrahedron Lett., 1999, 40, 1775–1778.
J. Areephong, J. H. Hurenkamp, M. T. W. Milder, A. Meetsma, J. L. Herek, W. R. Browne and B. L. Feringa, Photoswitchable sexithiophene-based molecular wires, Org. Lett., 2009, 11, 721–724.
M. N. Roberts, J. K. Nagle, J. G. Finden, N. R. Branda and M. O. Wolf, Linker-dependent metal-sensitized photoswitching of dithienylethenes, Inorg. Chem., 2009, 48, 19–21.
V. Lemieux and N. R. Branda, Reactivity-gated photochromism of 1,2-dithienyl-ethenes for potential use in dosimetry applications, Org. Lett., 2005, 7, 2969–2972.
X. L. Meng, W. H. Zhu, Q. Zhang, et al., Novel bisthienylethenes containing naphthalimide as the center ethene bridge: photochromism and solvatochromism for combined NOR and INHIBIT logic gates, J. Phys. Chem. B, 2008, 112, 15636–15645.
J. A. Gan, L. Sanguinet and J. L. Pozzo, Dyads and triads based on dithienylethene and indolino[2,1-b]oxazolidine, Mol. Cryst. Liq. Cryst., 2005, 430, 37–43.
Y. Chen, D. X. Zeng, N. Xie and Y. Z. Dang, Study on photochromism of diarylethenes with a 2,5-dihydropyrrolebridging unit: a convenient preparation of 3,4-diarylpyrroles from 3,4-diaryl-2,5-dihydropyrroles, J. Org. Chem., 2005, 70, 5001–5005.
S. Z. Pu, G. Liu, L. Shen and J. K. Xu, Efficient synthesis and properties of isomeric photochromic diarylethenes having a pyrrole unit, Org. Lett., 2007, 9, 2139–2142.
Q. F. Luo, S. H. Sheng, S. H. Cheng and H. Tian, Tunable luminescene of photochromic bithienylethenes containing triphenylamine, Aust. J. Chem., 2005, 58, 321–326.
J. Fabian and H. Hartmann, Light Absorption of Organic Colorants, Springer-Verlag, Berlin, 1980, pp. 24.
M. Irie, K. Sakemura, M. Okinaka and K. Uchida, Photochromism of dithienylethenes with electron-donating substituents, J. Org. Chem., 1995, 60, 8305–8309.
L. Giordano, T. M. Jovin, M. Irie, E. A. Jares-Erijman, Diheteroarylethenes as thermally stable photoswitchable acceptors in photochromic fluorescence resonance energy transfer (pcFRET), J. Am. Chem. Soc., 2002, 124, 7481–7489.
M. Frigoli, G. H. Mehl, The enhancement of photoswitching in a diarylethene derivative by the incorporation of cyanobiphenyl groups, Chem. Commun., 2004, 818–819
T. Kawai, T. Sasaki, M. Irie, A photoresponsive laser dye containing photochromic dithienylethene units, Chem. Commun., 2001, 711–712.
A. J. Myles, B. Gorodetsky and N. R. Branda, Photoregulation of luminescence quenching in photochromic porphyrin- phenoxynaphthacene-quinone copolymers, Adv. Mater., 2004, 16, 922–925.
M. Frigoli and G. H. Mehl, Modulation of the absorption, fluorescence, and liquid-crystal properties of functionalised diarylethene derivatives, Chem.-Eur. J., 2004, 10, 5243–5250.
H. H. Liu and Y. Chen, Construction and properties of multi-addressable switching system based on a photochromic diarylethene, J. Mater. Chem., 2009, 19, 706–709.
H. Tian, B. Qin, R. X. Yao, X. L. Zhao and S. J. Yang, A single photochromic molecular switch with four optical outputs probing four inputs, Adv. Mater., 2003, 15, 2104–2107.
Author information
Authors and Affiliations
Corresponding author
Additional information
This paper is part of a themed issue on synthetic and natural photoswitches.
Electronic supplementary information (ESI) available: Details of the synthetic procedures and 1H NMR spectral data for compounds 1′-3′, and the optimized conformations of all six trans- and cis-isomers. See DOI: 10.1039/b9pp00088g
Rights and permissions
About this article
Cite this article
Luo, Q., Liu, Y., Li, X. et al. Facile synthesis and characterization of new photochromic trans-dithienylethenes functionalized with pyridines and fluorenes. Photochem Photobiol Sci 9, 234–238 (2010). https://doi.org/10.1039/b9pp00088g
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1039/b9pp00088g