Abstract
Photochromic molecules are potentially applicable to the optical module for molecular switches and sensors. Herein, we report on a novel photochromic vinylpyrene-substituted 2’-deoxyguanosine analogue (VPy G) that undergoes the reversible E–Z isomerization accompanied with a unique “on–off” fluorescence switching. The highly fluorescent E-isomer was rapidly converted to the non-fluorescent Z-isomer under visible light irradiation (>420 nm). Conversely, when the Z-isomer was illuminated with UV-light (∼365 nm), Z- to E-isomerization also took place rapidly. Furthermore, such reversible photoisomerization was repeated more than 10 times without any side reaction. The drastic and reversible fluorescence change of the photochromic guanine base VPy G might be useful for molecular devices.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Feringa BL (2007) The art of building small: from molecular switches to molecular motors. J Org Chem 72:6635–6652
Green JE, Choil JW, Boukai A et al (2007) A 160-kilobit molecular electronic memory patterned at 1011 bits per square centimetre. Nature 445:414–417
Balzani V, Credi A, Venturi M (2003) Molecular devices and machines: a journey into the nano world. Wiley-VCH, Weinheim
Irie M, Mrozek T, Daub J et al (2001) In: Feringa BL (ed) Molecular switches. Wiley-VCH, Weinheim
Irie M (2000) Diarylethenes for memories and switches. Chem Rev 100:1685–1716
Hein B, Willig KI, Hell SW (2008) Stimulated emission depletion (STED) nanoscopy of a fluorescent protein-labeled organelle inside a living cell. Proc Natl Acad Sci USA 105:14271–14276
Andresen M, Stiel AC, Fölling J et al (2008) Photoswitchable fluorescent proteins enable monochromatic multilabel imaging and dual color fluorescence nanoscopy. Nat Biotechnol 26:1035–1040
Folling J, Belov V, Kunetsky R et al (2007) Photochromic rhodamines provide nanoscopy with optical sectioning. Angew Chem Int Ed 46:6266–6270
Milstein D, Stille JK (1978) A general, selective, and facile method for ketone synthesis from acid chlorides and organotin compounds catalyzed by palladium. J Am Chem Soc 100:3636–3638
Stille JK (1986) The palladium-catalyzed cross-coupling reactions of organotin reagents with organic electrophiles [new synthetic methods (58)]. Angew Chem Int Ed Engl 25:508–524
Conti I, Marchioni F, Credi A et al (2007) Cyclohexenylphenyldiazene: a simple surrogate of the azobenzene photochromic unit. J Am Chem Soc 129:3198–3210
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2010 Springer
About this paper
Cite this paper
Matsumoto, K., Saito, Y., Saito, I., Morii, T. (2010). Light Energy Induced Fluorescence Switching Based on Novel Photochromic Nucleosides. In: Yao, T. (eds) Zero-Carbon Energy Kyoto 2009. Green Energy and Technology. Springer, Tokyo. https://doi.org/10.1007/978-4-431-99779-5_29
Download citation
DOI: https://doi.org/10.1007/978-4-431-99779-5_29
Publisher Name: Springer, Tokyo
Print ISBN: 978-4-431-99778-8
Online ISBN: 978-4-431-99779-5
eBook Packages: EngineeringEngineering (R0)