Improving the stability of photochromic fluorinated indolylfulgides

Islamova, Nadezhda I.; Chen, Xi; García, Sandra Sánchez; Guez, Ghislaine; Silva, Yenia; Lees, Watson J.

doi:10.1016/j.jphotochem.2007.10.006

Cited by 23 publications

(45 citation statements)

References 26 publications

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“…The UV-vis absorption spectra of 1 , 2 , and 3 were measured in toluene (Fig. 1) as toluene is the standard solvent for studying indolylfulgides/fulgimides (Table 1) [4–7,36]. Monomers and polymers of 3-indolylfulgides/fulgimides have very similar absorption maxima, as was the case for 2-indolylfulgide/fulgimides [17].…”

Section: Resultsmentioning

confidence: 99%

Photochromic copolymers containing 3-indolylfulgides/indolylfulgimides: Synthesis and photochemical properties in toluene and as films

Islamova

Chen

Fan

et al. 2013

Polymer Degradation and Stability

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Photochromic indolylfulgimides covalently attached to polymers have beneficial properties for optical switching. A 3-indolylfulgide and two 3-indolylfulgimides with one or two polymerizable styrene groups attached on the nitrogen atom(s) were synthesized. Copolymerization with methyl methacrylate (MMA) provided linear copolymers (one styrene group) or a cross-linked copolymer (two styrene groups). The properties of the monomers and copolymers in toluene or as thin films were characterized. The new copolymers were photochromic (reversible Z-to-C isomerization), absorbed visible light, and revealed good thermal and photochemical stability. At room temperature, all copolymer films showed no loss of absorbance after 5 weeks. At 80 °C in either toluene or as films, the Z-forms copolymers were less stable than the C-form copolymers, which showed little or no degradation after 400 h. The degradation rate due to repeated ring-closing – ring opening cycles was less than 3% per 100 cycles. The cross-linked copolymer showed photochemical stability comparable to monomeric fulgides in toluene, <1% per 100 cycles. In general, the properties of the linear and cross-linked copolymers were similar to the corresponding monomers in toluene. In films, the conformations of the Z-form were restricted due to the matrix indicating that the preparation of films from the C-form is advantageous.

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Section: Resultsmentioning

confidence: 99%

Photochromic copolymers containing 3-indolylfulgides/indolylfulgimides: Synthesis and photochemical properties in toluene and as films

Islamova

Chen

Fan

et al. 2013

Polymer Degradation and Stability

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show abstract

“…[49][50][51][52] The most photochemically stable fulgide, a fluorinated indolylfulgide synthesized by Lees et al undergoes 10,000 photochemical cycles (back and forth conversion between the two key forms) before degrading by 13% in toluene. …”

Section: -48mentioning

confidence: 99%

“…52 Optimization in almost all cases has been performed in aprotic solvents. However, the properties of fulgides or fulgimides in aqueous solutions have not been thoroughly examined.…”

Section: -52mentioning

confidence: 99%

“…49,52,71 Previously, the thermal stability of fulgides and fulgimides was examined in toluene at 80 °C. 40,41,64 Therefore, the thermal stability of 10Z and 10C was determined under these conditions.…”

Section: Thermal Stabilitymentioning

confidence: 99%

“…49 In toluene, the most stable fulgide reported to date can be switched back and forth over 10,000 times before degrading by 13% 52 although for most fulgides the number is less. 51,64 In the case of fluorinated indolylfulgimides, a previous study indicated that they can be cycled back and forth between 700 and 3,000 times in toluene before degrading by 20%.…”

Section: Photochemical Stabilitymentioning

confidence: 99%

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