Solvatochromic and rigidochromic fluorescent probes based on D–π-A diaryl ethylene and butadiene derivatives for UV-curing monitoring

Peinado, C.; Salvador, Enrique F.; Catalina, F.; Lozano, Ángel E.

doi:10.1016/s0032-3861(00)00569-3

Cited by 38 publications

(34 citation statements)

References 29 publications

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“…The fluorescence maximum shift behaviour of 2OHDEANS is different in L350 although a change in the trend is observed at the same conversion (30%). The photophysical behaviour of 2OHDEANS in comparison with DMANS has been previously reported [18] and the presence of a hydroxyl group along with a pre-twisted geometry of the ground state of this molecule was related to the observed low solvatochromic effect. Preferential solvation of this fluorescent probe with methacrylic monomers by means of H-bonds provides additional stabilisation and this fact can induce less sensitivity mainly during the first stage of polymerisation.…”

Section: Fluorescence For Monitoring the Uv-curing Of Acrylic Adhesivesmentioning

confidence: 64%

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Fluorescent Probes for Monitoring the UV Curing of Acrylic Adhesives, 1. FTIR and Fluorescence in Real Time

Peinado¹,

Salvador

Baselga

et al. 2001

Macromol. Chem. Phys.

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The use of the fluorescence technique for monitoring the UV‐curing of two polyurethane‐based adhesives containing acrylic monomers is described in this paper. The increase of the fluorescence intensity as well as the maximum wavelength shift on emission was measured in real time during the photopolymerisation process. The established relationship between fluorescence and conversion allowed monitoring of the course of the process beyond vitrification. In that sense, all the fluorescent probes studied were sensitive to the formulation curing and in some cases, the range of conversions in which they were useful was limited by their size and probably, by the free volume fraction in the polymeric matrix. Moreover, polymerisation rates were obtained from fluorescent kinetic profiles and used to carry out a comparative study of the different photosensitive formulations. The real time FTIR (RTIR) results show the highest photoinitiation efficiency of the photoinitiator 2‐benzyl‐2‐N,N‐dimethylamino‐1‐(4‐morpholinophenyl)‐1‐butanone (Irgacure 369) compared to that of 2,2‐dimethoxy‐2‐phenylacetophenone (Irgacure 651). The limitation of RTIR method for monitoring slow post‐reactions was overcome by the use of the fluorescence‐based method. Thus, a fluorescence intensity increase and a blue‐shift of the emission band were measured after the limiting conversion was attained. Dynamic mechanical analysis showed that the glass transition temperature of the polymer increases during prolonged exposure to irradiation confirming the increase of the system rigidity.

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Section: Fluorescence For Monitoring the Uv-curing Of Acrylic Adhesivesmentioning

confidence: 64%

“…The synthesis of these compounds is described elsewhere. [18,19] Also, four fluorescent commercial probes, from Aldrich, ( …”

Section: Fluorescent Probes and Acrylic Adhesivesmentioning

confidence: 99%

Fluorescent Probes for Monitoring the UV Curing of Acrylic Adhesives, 1. FTIR and Fluorescence in Real Time

Peinado¹,

Salvador

Baselga

et al. 2001

Macromol. Chem. Phys.

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“…[28] Push-pull conjugated compounds form an intermediate class. [29][30][31] Their ground-state dipole moments are large enough to induce a solvent polarization which interacts more strongly with the molecules in the excited state because the dipole moments are in the same direction and the excited-state dipole moment is larger, which explains why there is a modest solvatochromic shift in absorption. The fluorescence solvatochromic shift is larger than the shift in absorption because it is driven by the larger excitedstate dipole moment.…”

Section: Discussionmentioning

confidence: 99%

Paradoxical Solvent Effects on the Absorption and Emission Spectra of Amino‐Substituted Perylene Monoimides

Zoon

Brouwer

2005

ChemPhysChem

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In N-(2,5-di-tert-butylphenyl)-9-pyrrolidinoperylene-3,4-dicarboximide (5PI) the absorption and emission spectra display large solvatochromic shifts, but, remarkably, the Stokes shift is practically independent of solvent polarity. This unique behavior is caused by the extraordinarily large ground-state dipole moment of 5PI, which further increases upon increasing the solvent polarity, whereas the excited-state dipole moment is less solvent dependent. In the corresponding piperidine compound, 6PI, this effect is much less important owing to the weaker coupling between the amino group and the aromatic imide moiety, and in the corresponding naphthalimide, 5NI, it is absent. The latter shows the conventional solvatochromic behavior of a push-pull substituted conjugated system, that is, minor shifts in absorption and a larger change in the emission energy with solvent polarity.

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“…4 shows the fluorescence spectra of NBD-NEt 2 during the polymerization of HDDA photoinitiated by TMBAPO at 40 8C under a nitrogen atmosphere. It is important to note that fluorescence is collected at the polymerization temperature (40 8C), thus, fluorescence changes are related to changes in the free volume fraction during UV-curing [15]. As free volume fraction depends on temperature more reliable correlation can be established here than when fluorescence is collected at room temperature.…”

Section: Fluorescence Monitoring Of Multifunctional (Meth)acrylates Pmentioning

confidence: 99%

Following in situ photoinitiated polymerization of multifunctional acrylic monomers by fluorescence and photocalorimetry simultaneously

Peinado

Alonso

Salvador

et al. 2002

Polymer

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The photoinitiated polymerization of multifunctional (meth)acrylic monomers was simultaneously monitored in real time by fluorescence and differential scanning calorimetry. As the curing proceeds, the fluorescence emission changes due to an increase in the viscosity of the microenvironment. A good correlation between fluorescence intensity and degree of conversion was established by using two different fluorescent probes, each having the same fluorophore, dialkylamino derivatives of 7-nitro-2-oxa-1,3-diazol. One of the probes contains an acrylic moiety which can react with the monomers labelling the formed network. The use of the first moment of fluorescence is presented as a suitable methodology to avoid experimental fluctuations. Furthermore, the influence of the length of the spacer between the acrylic groups in the polymerization reaction kinetics and fluorescence changes has been also discussed in terms of reaction diffusion controlled termination kinetics and free volume fraction. It was concluded that the fluorescence method is a powerful tool to study the kinetics of photopolymerization of multifunctional monomers.

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Solvatochromic and rigidochromic fluorescent probes based on D–π-A diaryl ethylene and butadiene derivatives for UV-curing monitoring

Cited by 38 publications

References 29 publications

Fluorescent Probes for Monitoring the UV Curing of Acrylic Adhesives, 1. FTIR and Fluorescence in Real Time

Fluorescent Probes for Monitoring the UV Curing of Acrylic Adhesives, 1. FTIR and Fluorescence in Real Time

Paradoxical Solvent Effects on the Absorption and Emission Spectra of Amino‐Substituted Perylene Monoimides

Following in situ photoinitiated polymerization of multifunctional acrylic monomers by fluorescence and photocalorimetry simultaneously

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