Photo-reversible Pb2+-complexation of thermosensitive poly(N-isopropyl acrylamide-co-spiropyran acrylate) in water

Suzuki, Takayuki; Kato, Tatsuya; Shinozaki, Hiraku

doi:10.1039/b407342h

“…[19,20] The as-preScheme 1. Supramolecular complex (composed of photosensitive bcyclodextrin and RhB) and photoreversible fluorescence modulation.…”

mentioning

confidence: 99%

Photoreversible Fluorescence Modulation of a Rhodamine Dye by Supramolecular Complexation with Photosensitive Cyclodextrin

Wu¹,

Luo²,

Zeng³

et al. 2007

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Materials with properties that can be optically modulated are of high interest in many scientific areas, including biotechnology and optics.[1] Photosensitive-in particular photochromic-compounds can be used to achieve this purpose, as they can be converted reversibly by light between two states with different spectroscopic properties. [2][3][4][5] This attribute can then be used to modulate or switch various functions at the molecular or supramolecular level by using light as a trigger. Spiropyran, a promising photochromic compound, undergoes reversible structural transformations in response to external inputs, such as light. [4,6,7] This special property of the spiropyran molecules was used to construct complex, optically controlled integrated logic gates and molecular switches composed of dyad or triad molecules with spiropyran as one of their units. [8][9][10] In this dyad or triad method, the modulation of various photonic or optoelectronic processes was usually realized by fluorescence quenching through energy transfer. In this approach to a light-controlled molecular switch or logic gate, several issues still need to be addressed: Firstly, the specific fluorophore must be covalently linked to the spiropyran molecule (or linked to it through a spacer) to form the dyad or the triad; hence, in this approach, only one dyad or triad can be used for a specific application. Secondly, selfquenching is still observed as a result of the self-aggregation of the fluorophore moieties. Thirdly, the dyads or triads are usually hydrophobic, which limits their applications in hydrophilic environments; in addition, they lack the necessary biocompatibility for applications in the fields of biotechnology.It is well known that cyclodextrin (CD) can form supramolecular inclusion complexes with small-molecule chromophore compounds that fit into its 5-8 cavity; [11][12][13] in this way, the fluorescence intensity, biocompatibility, and photostability of the guest chromophore compounds can be enhanced. [14,15] Herein, we synthesized photosensitive cyclodextrin (CDSP) by covalently attaching spiropyran moieties onto b-CD. Rhodamine B [16][17][18] (RhB) was used as a model fluorophore to form a supramolecular complex with the CDSP, and photoreversible fluorescence modulation was thus realized. This strategy is easily achievable, and the guest rhodamine molecules can be readily replaced by other chromophore compounds. In addition, the self-quenching of RhB can be decreased by supramolecular complexation. The strategy could provide a facile method for reversible fluorescence modulation, controlled by light, for a wide range of chromophores, which is essential in applications such as reversible bioimaging. At the same time, the chromophore complexes will have the necessary biocompatibility and hydrophilicity for applications in the field of biotechnology because of the presence of the oligosaccharide cyclodextrin.Photosensitive b-cyclodextrin was synthesized and based on mass spectrometry (MS), high-performance liquid chromatography (H...

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“…[4][5][6][7][8][9][10][11][12][13][14][15] However, the synthesis and characterization of oligomers or polymers containing spiropyran moieties in the main backbone have not been well investigated. [16][17][18][19][20][21][22][23] Herein, we report the synthesis and characterization of conjugated bis-spiropyran derivatives.…”

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confidence: 99%

Synthesis and Characterizations of Bis-Spiropyran Derivatives

Lee¹,

Ji²,

Kang³

2012

Bulletin of the Korean Chemical Society

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We synthesized three different derivatives of bis-spiropyran using simple organic reactions with high yields. BSP1, a derivative of bis-spiropyran having a connection at the position 6' and BSP2, a derivative of bisspiropyran having a connection at the position 5 and BSP3, a derivative of bis-spiropyran containing a dithienylethene group between two spiropyran moieties were synthesized. The optical properties of BSPs were characterized. UV-Vis spectra showed that BSPs exhibit reversible photo-isomerization and the efficiency of photo-isomerization is highly dependent on the position of nitro group. BSPs having nitro group at para position of hydroxy group showed the higher efficiency of photo-isomerization that the one having nitro group at ortho position. The optical microscope images obtained under ultraviolet or visible light exposure demonstrated that the formation of nanorods can be reversibly controlled by optical signal.

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“…[19,20] The as-pre- The formation of a complex between RhB and the CDSP-2 was verified by 2D NMR experiments (see the Supporting Information). [19,20] The as-pre- The formation of a complex between RhB and the CDSP-2 was verified by 2D NMR experiments (see the Supporting Information).…”

mentioning

confidence: 90%

“…In this approach to a light-controlled molecular switch or logic gate, several issues still need to be addressed: Firstly, the specific fluorophore must be covalently linked to the spiropyran molecule (or linked to it through a spacer) to form the dyad or the triad; hence, in this approach, only one dyad or triad can be used for a specific application. [19,20] The as-pre-Scheme 1. Thirdly, the dyads or triads are usually hydrophobic, which limits their applications in hydrophilic environments; in addition, they lack the necessary biocompatibility for applications in the fields of biotechnology.…”

mentioning

confidence: 99%

Photoreversible Fluorescence Modulation of a Rhodamine Dye by Supramolecular Complexation with Photosensitive Cyclodextrin

Wu

¹

,

Luo

²

,

Zeng

³

et al. 2007

View full text Add to dashboard Cite

Materials with properties that can be optically modulated are of high interest in many scientific areas, including biotechnology and optics.[1] Photosensitive-in particular photochromic-compounds can be used to achieve this purpose, as they can be converted reversibly by light between two states with different spectroscopic properties. [2][3][4][5] This attribute can then be used to modulate or switch various functions at the molecular or supramolecular level by using light as a trigger. Spiropyran, a promising photochromic compound, undergoes reversible structural transformations in response to external inputs, such as light. [4,6,7] This special property of the spiropyran molecules was used to construct complex, optically controlled integrated logic gates and molecular switches composed of dyad or triad molecules with spiropyran as one of their units. [8][9][10] In this dyad or triad method, the modulation of various photonic or optoelectronic processes was usually realized by fluorescence quenching through energy transfer. In this approach to a light-controlled molecular switch or logic gate, several issues still need to be addressed: Firstly, the specific fluorophore must be covalently linked to the spiropyran molecule (or linked to it through a spacer) to form the dyad or the triad; hence, in this approach, only one dyad or triad can be used for a specific application. Secondly, selfquenching is still observed as a result of the self-aggregation of the fluorophore moieties. Thirdly, the dyads or triads are usually hydrophobic, which limits their applications in hydrophilic environments; in addition, they lack the necessary biocompatibility for applications in the fields of biotechnology.It is well known that cyclodextrin (CD) can form supramolecular inclusion complexes with small-molecule chromophore compounds that fit into its 5-8 cavity; [11][12][13] in this way, the fluorescence intensity, biocompatibility, and photostability of the guest chromophore compounds can be enhanced. [14,15] Herein, we synthesized photosensitive cyclodextrin (CDSP) by covalently attaching spiropyran moieties onto b-CD. Rhodamine B [16][17][18] (RhB) was used as a model fluorophore to form a supramolecular complex with the CDSP, and photoreversible fluorescence modulation was thus realized. This strategy is easily achievable, and the guest rhodamine molecules can be readily replaced by other chromophore compounds. In addition, the self-quenching of RhB can be decreased by supramolecular complexation. The strategy could provide a facile method for reversible fluorescence modulation, controlled by light, for a wide range of chromophores, which is essential in applications such as reversible bioimaging. At the same time, the chromophore complexes will have the necessary biocompatibility and hydrophilicity for applications in the field of biotechnology because of the presence of the oligosaccharide cyclodextrin.Photosensitive b-cyclodextrin was synthesized and based on mass spectrometry (MS), high-performance liquid chromatography (H...

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Photo-reversible Pb2+-complexation of thermosensitive poly(N-isopropyl acrylamide-co-spiropyran acrylate) in water

Abstract: Photo-reversible Pb2+-complexation in a purely aqueous environment exhibiting a thermosensitive phase transition at a lower critical solution temperature was achieved using a synthetic copolymer composed of N-isopropyl acrylamide and spiropyran acrylate.

Cited by 53 publications

References 6 publications

Photoreversible Fluorescence Modulation of a Rhodamine Dye by Supramolecular Complexation with Photosensitive Cyclodextrin

Photoreversible Fluorescence Modulation of a Rhodamine Dye by Supramolecular Complexation with Photosensitive Cyclodextrin

Synthesis and Characterizations of Bis-Spiropyran Derivatives

Photoreversible Fluorescence Modulation of a Rhodamine Dye by Supramolecular Complexation with Photosensitive Cyclodextrin

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