Photochemically Induced Fluorescence Control with Intermolecular Energy Transfer from a Fluorescent Dye to a Photochromic Diarylethene in a Polymer Film

Murase, Sachiko; Teramoto, Madoka; Furukawa, Hidemitsu; Miyashita, Yoshiharu; Horie, Kazuyuki

doi:10.1021/ma021276p

Cited by 62 publications

(39 citation statements)

References 26 publications

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“…1 H NMR spectroscopy of the polymers show broadened peaks, as expected for the copolymers. The relative intensities of the broadened peaks in the spectra correspond to the anticipated porphyrin/PNQ ratios (4:1 for P1a, 1:1 for P2a, and 1:4 for P3a).…”

supporting

confidence: 59%

“…It is particularly appealing for use in the latter application because the ªON/OFFº properties of the polymers can be used to store and process information, with high sensitivity and resolution. [1] Luminescence can be regulated by using photochromic compounds, [2] which are compounds that interconvert between two isomeric forms when stimulated by two different wavelengths of light. [3] Molecules with this behavior are some of the best contenders for use in erasable memory media, where each isomer of the photochromic compound can represent ª0º or ª1º of a digital code.…”

mentioning

confidence: 99%

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Photoregulation of Luminescence Quenching in Photochromic Porphyrin–Phenoxynaphthacene‐ quinone Copolymers

Myles

Gorodetsky

Branda³

2004

Advanced Materials

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Photoswitchable luminescence in polymers is a versatile physical change useful in fluorescent sensor and optoelectronic device applications. It is particularly appealing for use in the latter application because the ªON/OFFº properties of the polymers can be used to store and process information, with high sensitivity and resolution.[1] Luminescence can be regulated by using photochromic compounds, [2] which are compounds that interconvert between two isomeric forms when stimulated by two different wavelengths of light. [3] Molecules with this behavior are some of the best contenders for use in erasable memory media, where each isomer of the photochromic compound can represent ª0º or ª1º of a digital code. [4] Photochromic compounds that affect the luminescence intensities of neighboring chromophores help circumvent one of the most serious problems associated with the use of photochromic compounds in memory media: the concomitant erasing of the stored information during a detection event that relies on measuring variations in absorption intensities.[5]Photoregulated emission is possible using photochromic compounds only when there is a discriminating interaction between the excited state of the fluorescent dye and the ground state of one of the photochromic isomers. This interaction can be through photoinduced energy or electron transfer processes. Photochromic phenoxynaphthacenequinone (PNQ) derivatives undergo thermally irreversible isomerization reactions (1a > 1b; see below) with a high degree of fatigue resistance.[6] We have recently described the first example of photoregulation of luminescence in a hydrogen-bonded porphyrin±quinone system by reversibly changing the redox properties of the electron acceptor in a donor±acceptor pair.[7]The quenching of luminescence can be regulated in this supramolecular complex by reversibly varying the ability of the photochromic PNQ to act as an electron acceptor species. Isomer 1b can be reduced at a significantly less negative potential than 1a and, thus, acts as a better electron acceptor to suppress the fluorescence read-out signal from the porphyrin through what we have attributed to a photoinduced electron transfer mechanism, although this mechanism has yet to be unequivocally proven.One approach to extend this photoregulation to polymeric systems is to evenly disperse both the fluorescent dye and the photochromic compound in the polymer film. This strategy has been shown to work, [1a] but is potentially plagued by problems such as phase separation, crystallization, and concentration gradients when the amounts of the additives become too great. We have reported that ring-opening metathesis polymerization (ROMP) of strained bicyclic olefins is an excellent polymerization method for photochromic compounds, due to its mild reaction conditions, functional group compatibility, and control over polymer chain length.[8] Polymers generated using this technique are less susceptible to the problems associated with polymers doped with the photochromic components. Here, we re...

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confidence: 59%

mentioning

confidence: 99%

Photoregulation of Luminescence Quenching in Photochromic Porphyrin–Phenoxynaphthacene‐ quinone Copolymers

Myles

Gorodetsky

Branda³

2004

Advanced Materials

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“…In dilute solution, only intramolecular energy transfer usually exists. However, the intermolecular energy transfer 29 from light emitting molecules to the surrounding closed-form DTE molecules contributes significantly to the fluorescence quenching because of the much larger molecular packing density in solid film, especially in pure film with a huge quenching ratio closed to N (Supplementary Table 2). In PMA film, the emission peak is about 634 nm, which is similar to solid film (640 nm), whereas it is 580 nm for PMMA film.…”

Section: Resultsmentioning

confidence: 99%

A trident dithienylethene-perylenemonoimide dyad with super fluorescence switching speed and ratio

et al. 2014

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Photoswitchable fluorescent diarylethenes are promising in molecular optical memory and photonic devices. However, the performance of current diarylethenes is far from satisfactory because of the scarcity of high-speed switching capability and large fluorescence on-off ratio. Here we report a trident perylenemonoimide dyad modified by triple dithienylethenes whose photochromic fluorescence quenching ratio at the photostationary state exceeds 10,000 and the fluorescence quenching efficiency is close to 100% within seconds of ultraviolet irradiation. The highly sensitive fluorescence on/off switching of the trident dyad enables recyclable fluorescence patterning and all-optical transistors. The prototype optical device based on the trident dyad enables the optical switching of incident light and conversion from incident light wavelength to transmitted light wavelength, which is all-optically controlled, reversible and wavelength-convertible. In addition, the trident dyad-staining block copolymer vesicles are observed via optical nanoimaging with a sub-100 nm resolution, portending a potential prospect of the dithienylethene dyad in super-resolution imaging.

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“…The polymer cast fi lms showed absorption bands in a longer wavelength region than those of the CHCl 3 solutions (Figure 2 b) because the effective conjugated length of the polymer main chains were increased in the solid state. More specifi cally, the absorption bands of P1 − P7 were red-shifted by 11,0,19,14,11,35, and 40 nm, respectively (see Table 2 ). It is worth noting that the thienylene-containing polymers of P3 , P4 , P6 , and P7 exhibited larger red shifts in absorption than those of the thienylene-free polymers P1 , P2 , and P5 .…”

Section: Absorption and Fluorescence Of P1−p7 Solutions And Cast Filmsmentioning

confidence: 99%

Dynamic Control of Full‐Colored Emission and Quenching of Photoresponsive Conjugated Polymers by Photostimuli

Watanabe

Hayasaka

Miyashita

et al. 2015

Adv Funct Materials

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wileyonlinelibrary.comand aggregation-enhanced emission (AEE) characteristics were reported in selected ACPs. [14][15][16] Therefore, it is of great interest to investigate ACPs in the aggregated state that are quite different from those the isolated chain state.The polymer nanosphere solution can be treated as an intermediate state between a solution state and a solid fi lm state because the polymer nanoparticles uniformly disperse in a solvent, similar to their behavior in solution, whereas the polymer chains aggregate with each other, similarly to their behavior in a solid fi lm. In other words, the polymer nanosphere solution can be regarded as a dispersed nano-ordered crystalline polymer system. This bilateral character of the nanosphere solution causes the polymer to exhibit high processability and fl uidity as well as aggregation effects. In addition, the polymer nanosphere solution enables quantitative analysis of the aggregated state of polymers from the spectroscopic point of view. Hence, the polymer nanosphere solution is useful for understanding the aggregation effect on ACPs as compared with the solution and solid fi lm states.Dynamic control of the fl uorescence of ACPs using an external light stimulus is of particular interest because such photoresponsive polymers are essential for next-generation optoelectronic materials. Dithienylethene (DE) derivatives [17][18][19][20] are one class of the most attractive photoresponsive materials because of their outstanding fatigue resistance, thermal stability, and ability to undergo conformational changes between open and closed forms via photoisomerization, and therefore they are regarded as promising materials for the fabrication of photodynamically controllable luminescent devices [ 21,22 ] as well as photodynamically color-tunable systems. [23][24][25][26][27] The DE derivatives are also known to display luminescent color changes via photoisomerization. [ 20,[28][29][30][31][32][33][34][35][36][37] Similarly, conjugated polymers that contain DE moieties in the polymer backbones exhibit photochromism. [ 20,[38][39][40][41] The chromism in both absorption and luminescence of the conjugated polymers is attributed to structural changes in the conjugated backbones resulting from the DE photoisomerization. Hence, it is necessary to properly design the molecular structure to realize the desired switching behavior and fl uorescent colors.It is well known that in ACP nanoparticles doped with luminescent dopants, the ACP fl uorescence is almost completely quenched and the fl uorescence of the dopant is mainly

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Photochemically Induced Fluorescence Control with Intermolecular Energy Transfer from a Fluorescent Dye to a Photochromic Diarylethene in a Polymer Film

Cited by 62 publications

References 26 publications

Photoregulation of Luminescence Quenching in Photochromic Porphyrin–Phenoxynaphthacene‐ quinone Copolymers

Photoregulation of Luminescence Quenching in Photochromic Porphyrin–Phenoxynaphthacene‐ quinone Copolymers

A trident dithienylethene-perylenemonoimide dyad with super fluorescence switching speed and ratio

Dynamic Control of Full‐Colored Emission and Quenching of Photoresponsive Conjugated Polymers by Photostimuli

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