Abstract
Two approaches to prepare visible-light-sensitive diarylethene (DAE) derivatives are described. One is direct excitation of well-designed DAE derivatives with visible light and the other is indirect visible-light excitation to a reactive triplet state by a triplet energy transfer. The absorption spectra of both open- and closed-ring isomers of DAE are dependent not only on the aryl groups, but also on the ethene bridge. Introduction of dicyanoethene, maleic anhydride, or maleimide to the ethene bridge shifts the absorption bands of the open-ring isomers to the visible wavelength region. DAEs having an aromatic dye in the central reactive carbon atom were designed and their photochromic as well as fluorescence performance upon irradiation with visible light was studied. DAE-perylene di-imide dyad was found to undergo a photocyclization reaction upon irradiation with 532 nm laser light, where both the open- and the closed-ring isomers of DAE unit have no absorption band. Wavelength dependence of the photoreaction and oxygen effect revealed that the triplet state is responsible to the photocyclization reaction. Molecular design strategy described in this chapter will help to develop novel photochromic DAEs for advanced molecular probes in biological systems.
This is a preview of subscription content, log in via an institution to check access.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Dürr H, Bouas-Laurent H (2003) Photochromism molecules and systems. Elsevier, Amsterdam
Feringa BL, Browne WR (2011) Molecular switches, 2nd edn. Wiley-VCH, Weinheim
Irie M (2000) Diarylethenes for memories and switches. Chem Rev 100:1685–1716
Irie M, Fukaminato T, Matsuda K, Kobatake S (2014) Photochromism of diarylethene molecules and crystals: memories, switches, and actuators. Chem Rev 114:12174–12277
Hell SW (2007) Far-field optical nanoscopy. Science 316:1153–1158
Szymański W, Beierle JM, Kistemaker HAV, Velema WA, Feringa BL (2013) Reversible photocontrol of biological systems by the incorporation of molecular photoswitches. Chem Rev 113:6114–6178
Brieke C, Rohrbach F, Gottschalk A, Mayer G, Heckel A (2012) Light-controlled tools. Angew Chem Int Ed 51:8446–8476
Uchida K, Nakayama Y, Irie M (1990) Thermally irreversible photochromic systems. Reversible photocyclization of 1,2-bis(benzo[b]thiophen-3-yl)ethene derivatives. Bull Chem Soc Jpn 63:1311–1315
Sumi T, Kaburagi T, Morimoto M, Une K, Sotome H, Ito S, Miyasaka H, Irie M (2015) Fluorescent photochromic diarylethene that turns on with visible light. Org Lett 17:4802–4805
Irie M, Sayo K (1992) Solvent effects on the photochromic reactions of diarylethene derivatives. J Phys Chem 96:7671–7674
Ohsumi M, Hazama M, Fukaminato T, Irie M (2008) Photocyclization reaction of a diarylmaleimide derivative in polar solvents. Chem Commun 3281–3283
Irie M, Eriguchi T, Takada T, Uchida K (1998) Photochromism of diarylethene having thiophene oligomers as the aryl groups. Tetrahedron 53:12263–12271
Fukaminato T, Hirose T, Doi T, Hazama M, Matsuda K, Irie M (2014) Molecular design strategy toward diarylethenes that photoswitch with visible light. J Am Chem Soc 136:17145–17154
Tanifuji N, Irie M, Matsuda K (2005) New photoswitching unit for magnetic interaction: diarylethene with 2,5-bis(arylethynyl)-3-thienyl group. J Am Chem Soc 127:13344–13353
Odo Y, Matsuda K, Irie M (2006) pKa switching induced by the change in the p-conjugation system based on photochromism. Chem Eur J 12:4283–4288
Turro NJ, Ramamurthy V, Scaiano JC (2009) A theory of molecular organic photochemistry. In: Principles of molecular photochemistry: an introduction. University Science Books, Sausalito, CA, pp 319–382
Fredrich S, Göstl R, Herder M, Grubert L, Hecht S (2016) Switching diarylethenes reliably in both directions with visible light. Angew Chem Int Ed 55:1208–1212
Bléger D, Hecht S (2015) Visible-light-activated molecular switches. Angew Chem Int Ed 54:11338–11349
Mori K, Ishibashi Y, Matsuda H, Ito S, Nagasawa Y, Nakagawa H, Uchida K, Yokojima S, Nakamura S, Irie M, Miyasaka H (2011) One-color reversible control of photochromic reactions in a diarylethene derivative: three-photon cyclization and two-photon cycloreversion by a near-infrared femtosecond laser pulse at 1.28 μm. J Am Chem Soc 133:2621–2625
Wu T, Johnsen B, Qin Z, Morimoto M, Baillie D, Irie M, Branda NR (2015) Two-colour fluorescent imaging in organisms using self-assembled nano-systems of upconverting nanoparticles and molecular switches. Nanoscale 7:11263–11266
Jukes RTF, Adamo V, Hartl F, Belser P, De Cola L (2004) Photochromic dithienylethene derivatives containing Ru(II) or Os(II) metal units. Sensitized photocyclization from a triplet state. Inorg Chem 43:2779–2792
Murata R, Yago T, Wakasa M (2011) Cyclization reaction of diarylethene through the triplet excited state. Bull Chem Soc Jpn 84:1336–1338
Fukaminato T, Doi T, Tanaka M, Irie M (2009) Photocyclization reaction of diarylethene-perylenebisimide dyads upon irradiation with visible (>500 nm) light. J Phys Chem C 113:11623–11627
Fukaminato T, Doi T, Tamaoki N, Okuno K, Ishibashi Y, Miyasaka H, Irie M (2011) Single-molecule fluorescence photoswitching of a diarylethene-perylenebisimide dyad: non-destructive fluorescence readout. J Am Chem Soc 133:4984–4990
Fukaminato T (2011) Single-molecule fluorescence photoswitching: Design and synthesis of photoswitchable fluorescent molecules. J Photochem Photobiol C: Photochem Rev 12:177–208
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2017 Springer Japan KK
About this chapter
Cite this chapter
Fukaminato, T., Irie, M. (2017). Diarylethenes that Photoswitch with Visible Light. In: Yokoyama, Y., Nakatani, K. (eds) Photon-Working Switches. Springer, Tokyo. https://doi.org/10.1007/978-4-431-56544-4_8
Download citation
DOI: https://doi.org/10.1007/978-4-431-56544-4_8
Published:
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-56542-0
Online ISBN: 978-4-431-56544-4
eBook Packages: Chemistry and Materials ScienceChemistry and Material Science (R0)