Solvent Effect on the Photochemical Properties of Symmetrically Substituted <i>trans</i>-3,3‘,5,5‘-Tetramethoxystilbene

Hayakawa, Junpei; Ikegami, Machiko; Mizutani, Takuo; Wahadoszamen, Md.; Momotake, Atsuya; Nishimura, Yukio; Arai, Tatsuo

doi:10.1021/jp065075p

Cited by 20 publications

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“…Furthermore, the dipole moment in the excited state (® e =9.5 D) is larger than that in the ground state (® g = 2.5 D). 15 It should be noted here that the observed lifetime of 23 ns is the longest one in simply substituted stilbenes. 6 ] are ascribable to the existence of two different solvation environments as shown in Figure 6.…”

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“…We have found that trans-TMST has considerably long fluorescence lifetime of more than 10 ns in polar solvent such as acetonitrile and decreases with decreasing polarity of the solvent. 15 Thus, TMST was thought to be an appropriate compound to study the real viscosity of ionic liquid and the polarity of ionic liquid from the point of view of microviscosity and bulk viscosity. The measured viscosity of ionic liquid [bmim][PF 6 ] (260 cP) 16 used in these experiments as a solvent is much higher than that of acetonitrile (0.34 cP), 16 18 but is almost equivalent with the value of methanol (55.0).…”

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Photoisomerization and Fluorescence Characteristics of Tetramethoxystilbene in Ionic Liquid

Tamura¹,

Arai²

2011

Chemistry Letters

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Photochemical behavior of 3,3¤,5,5¤-tetramethoxystilbene (TMST) has been explored in ionic liquid. Two fluorescence components with the lifetime of 4.3 and 23.0 ns were observed for trans-TMST in ionic liquid solution. From this experimental evidence one could propose that ionic liquid may provide two different environments with highly different polarity, nonpolar and highly polar environments.We have been studying photoresponsive materials having C=C double bonds as a basic chromophore of photochemical reactions. 1 As to the usual aromatic compounds we have revealed that the photoisomerization properties such as quantum yield of isomerization and isomerization selectivity are controlled by the excited state energy of the substituent of the aromatic groups substituted at the C=C double bond. In order to develop different photoresponsive compounds we are interested in exploring more complex molecules such as high-molecularweight compounds as well as functionalized molecules by intermolecular 2 or intramolecular 3 5 hydrogen bonding. In the study of high-molecular-weight dendritic compounds, we have prepared water-soluble compounds related to unimolecular micelles as well as compounds soluble in organic solvent. Particularly, for water-soluble stilbene dendrimers we could afford nanoscale unimolecular compounds which have hydrophobic interior and hydrophilic exterior and found several unprecedented photochemical reactions such as highly selective almost one-way trans-to-cis photoisomerization in water. 6 Aromatic C=C compound with hydrogen bonding also exerted interesting photochemical properties showing one-way trans-to-cis isomerization induced by ultrafast intramolecular hydrogen atom transfer in the excited state. 7 As another approach to functionalizing molecules with C=C double bonds we are interested in introducing potentially ionic salts in photoresponsive compounds such as stilbene. Some of the work concerning photoresponsive ionic liquid has been published by us 8,9 for stilbene and by Kawai et al. 10,11 for azobenzene as chromophore. We should briefly mention that ionic liquid is fluid despite being composed of anions and cations and is very much different from inorganic salts which have considerably high melting point.In a previous paper, stilbene ionic liquids with imidazolium cation directly or indirectly attached to the benzene ring at the C=C double bond (Figure 1) have been prepared and it has been found that most of these ionic compounds are ionic liquids either at room temperature or below 100°C. 8,9 Furthermore, cis ionic liquids are all nonfluorescent and trans ionic liquids are all fluorescent and therefore, one can photochemically switch the fluorescence properties as well as morphology of either liquid or solid. Moreover, the stilbene-like compounds are easily isolated as pure cis-and trans-isomers and are stable at room temperature, and therefore we have proposed that the previously reported studies may help to understand the basic properties of stilbene ionic liquids and give some directi...

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Photoisomerization and Fluorescence Characteristics of Tetramethoxystilbene in Ionic Liquid

Tamura¹,

Arai²

2011

Chemistry Letters

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“…Besides porphyrins and phthalocyanines, there exist a few other types of fluorophores that can be used as the core of water‐soluble dendrimers. The fluorescence in water of the stilbene derivatives 7‐G n (Figure 4) was shown to be blue‐shifted with increasing generations ( λ em =424, 411, and 389 nm for 7‐G 0 , 7‐G 1 , and 7‐G 2 , respectively), indicating the decrease of the interaction between water and the excited state of stilbene, for higher generations 36. The symmetrically substituted perylene 8‐G n (Figure 4) has low fluorescence intensity in water, due to aggregation phenomena that depend on the overall steric requirements of the attached dendritic wedges and on hydrophobic interactions.…”

Section: Fluorescent Cores Of Dendrimersmentioning

confidence: 99%

Multicharged and/or Water‐Soluble Fluorescent Dendrimers: Properties and Uses

Caminade

Hameau

Majoral

2009

Chemistry A European J

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“…This data indicated that the excited singlet state of trans-TMST has a charge transfer (CT) character. Fluorescence lifetimes of trans-TMST were measured [87]. Effect of solvent polarity on photoisomerization of trans-4,4 0 -bis (benzoxazolyl) stilbene has been reported [86].…”

Section: Viscosity Effectmentioning

confidence: 99%

Stilbene Photoisomerization

2009

Stilbenes

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Solvent Effect on the Photochemical Properties of Symmetrically Substituted trans-3,3‘,5,5‘-Tetramethoxystilbene

Cited by 20 publications

References 31 publications

Photoisomerization and Fluorescence Characteristics of Tetramethoxystilbene in Ionic Liquid

Photoisomerization and Fluorescence Characteristics of Tetramethoxystilbene in Ionic Liquid

Multicharged and/or Water‐Soluble Fluorescent Dendrimers: Properties and Uses

Stilbene Photoisomerization

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