Order and Mobility of the Fluorescent Probe 1,6-Diphenylhexatriene in a Polyester Liquid Crystal Polymer

Arcioni, Alberto; Bacchiocchi, Corrado; D’Elia, Marcello; Tarroni, Riccardo; Zannoni, Claudio

doi:10.1080/10587250108025775

Cited by 3 publications

(2 citation statements)

References 34 publications

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“…Diphenylpolyenes are hydrophobic neutral organic bases that can be used to characterize the fluidity of micelles and cell membranes (Singh & Darshi, 2002), as well as amorphous phase transitions in drawn polyethylene rods (Everall et al, 1996) or polyester liquid crystals (Arcioni et al, 2001). To date, they have not been used as pH indicators, most likely because of their relative insolubility in water.…”

Section: Discussionmentioning

confidence: 99%

Comparison of two diphenyl polyenes as acid‐sensitive additives during the biodegradation of a thermoset polyester polyurethane coating

Shesham

Kelly

Burke

et al. 2021

J of Applied Microbiology

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Aims: Biochemical hydrolysis and chemical catalysis are involved in the successful biodegradation of polymers. In order to evaluate the potential separation between biochemical and chemical catalysis during the biodegradation process, we report the use of two diphenylpolyenes (DPPs), all trans-1,4-diphenylbutadiene (DPB) and all trans-1,6-diphenylhexatriene (DPH), as potential acid-sensitive indicators in polymers. Methods and Results: 1,4-Diphenylbutadiene and DPH (0.1% w/w) were melt-cast successfully with poly(ethylene succinate) hexamethylene (PES-HM) polyurethane (thermoset polyester polyurethane) coatings above 80℃. When these two DPP/ PES-HM coatings were exposed to a concentrated supernatant with significant esterase activity resulting from the growth of a recently isolated and identified strain of Tremellomycetes yeast (Naganishia albida 5307AI), the DPB coatings exhibited a measurable and reproducible localized decrease in the blue fluorescence emission in regions below where hydrolytic biodegradation was initiated in contrast with DPH blended coatings. The fluorescence changes observed in the biodegraded DPB coating were similar to exposing them to concentrated acids and not bases. Conclusions:Our experiments resulted in (1) a method to blend DPP additives into thermoset coatings, (2) the first report of the biodegradation of polyester polyurethane coating by N. albida, and (3) demonstration that hydrolytic supernatants from this strain generate acidic region within degrading polyester coatings using DPB as the indicator.Significance and Impact of the Study: Our experiments confirm that N. albida is an active polyester degrader and that DPB is a promising acid sensitive polymer coating additive.

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Section: Discussionmentioning

confidence: 99%

Comparison of two diphenyl polyenes as acid‐sensitive additives during the biodegradation of a thermoset polyester polyurethane coating

Shesham

Kelly

Burke

et al. 2021

J of Applied Microbiology

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“…These processes can be detected as: (1) absorption spectral changes, which sometimes show new absorption bands correlated to aggregates; 1,2 (2) negative deviation of Beer's law at the wavelengths related to monomers; [3][4][5][6][7][8][9][10] and (3) strong fluorescence diminution due to self-quenching of the excited states of the monomers that constitute the aggregate. [11][12][13][14] All-trans-1,6-diphenyl-1,3,5-hexatriene (DPH), a non-dye compound, is one of the most employed probes to investigate cell membranes, 15,16 polymer structures, 17 and micelle and liposome systems [18][19][20][21] due to its physical-chemical properties. DPH electronic transitions, such as light absorption and emission, are largely studied in organic solvents; [22][23][24][25][26][27] however, there are few reports on DPH in water-miscible organic solvent mixtures.…”

Section: Introductionmentioning

confidence: 99%

Self-Aggregation Processes of 1,6-Diphenyl-1,3,5-Hexatriene in Water/Ethanol Mixtures with High Water Percentages

Gracetto

Tessaro²,

Souza³

et al. 2011

Appl Spectrosc

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This work describes the behavior of 1,6-diphenyl-1,3,5-hexatriene (DPH) in ethanol/water mixtures. The dependence of DPH photophysical properties (absorption and fluorescence emission) on the water percentage in ethanol indicates that DPH undergoes self-aggregation processes in solvent conditions above a critical water content. Evidence such as an additional absorption band, Beer's law deviation, kinetic behavior, and other experimental results obtained from temperature variation and surfactant addition demonstrated the presence of several types of DPH aggregates. Resonance light scattering measurements proved that the aggregate grew in water-rich media by a self-catalyzed process.

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Origin of the vibrational structure of the first absorption band of cis/trans isomeric 1,6-diphenylhexatrienes by (TD)DFT calculations

Martin-Somer,

Catalán

2024

The Journal of Chemical Physics

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We present a detailed spectroscopic analysis of the first absorption band of the six possible conformers of 1,6-diphenyl-1,3,5-hexatriene, obtained by changing the configuration of trans double bonds to cis. To this end, we computed the absorption spectra using FCclasses 3.0 code. First, we assessed the performance of PBE0 and CAM-B3LYP density functional theory functionals with different basis sets to reproduce the experimental spectra. Additionally, we considered different models to compute the spectra. PBE0/def2tZVP with an adiabatic hessian model with internal coordinates yields results in very good agreement with experimental data. Subsequently, we analyzed the different contributions of vibronic transition to the spectral structure, correlating ground state conformation with spectral shape, and studied the effect of temperature on the absorption first band.

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Order and Mobility of the Fluorescent Probe 1,6-Diphenylhexatriene in a Polyester Liquid Crystal Polymer

Cited by 3 publications

References 34 publications

Comparison of two diphenyl polyenes as acid‐sensitive additives during the biodegradation of a thermoset polyester polyurethane coating

Comparison of two diphenyl polyenes as acid‐sensitive additives during the biodegradation of a thermoset polyester polyurethane coating

Self-Aggregation Processes of 1,6-Diphenyl-1,3,5-Hexatriene in Water/Ethanol Mixtures with High Water Percentages

Origin of the vibrational structure of the first absorption band of cis/trans isomeric 1,6-diphenylhexatrienes by (TD)DFT calculations

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