Synthesis and spectroscopic examination of various substituted 1,3-dibenzoylmethane, active agents for UVA/UVB photoprotection

Hubaud, Jean-Claude; Bombarda, Isabelle; Decome, Laetitia; Wallet, Jean‐Claude; Gaydou, Émile M.

doi:10.1016/j.jphotobiol.2008.05.004

Cited by 9 publications

(7 citation statements)

References 38 publications

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“…34 Williamson ether synthesis was used to prepare alkoxy-substituted ketone building blocks using a previously described method. 34 Data for PH 35 and PC1 35 are in accordance with previous reports.…”

Section: ■ Introductionsupporting

confidence: 87%

Supercooled Liquid β-Diketones with Mechanoresponsive Emission

et al. 2019

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Shear-induced crystallization of dyes in the amorphous state is an effective strategy for generating higher energy emission after mechanical perturbationa rare phenomenon in mechanoresponsive materials. Recently, we reported that a β-diketone with a 3,4,5-trimethoxy-substituted phenyl ring formed a stable supercooled liquid (SCL) phase after melting and cooling in air. To tune the lifetime of β-diketones in the SCL phase, a series of dyes with 3,4,5-trimethoxy-substituted phenyl rings were synthesized. Derivatives with naphthyl and phenyl rings were prepared in order to modulate crystallization through arene interactions. Additionally, dyes were substituted with alkoxy chains of varying length to promote crystallization through increased van der Waals interactions. Video screening in conjunction with differential scanning calorimetry and X-ray diffraction studies indicated that naphthyl-substituted derivatives exhibited increased melted state lifetimes and that increasing the alkoxy chain length can induce crystallization. Analysis of molecular packing of single crystals of PH, PC1, PC3, and PC5 revealed that the central para-substituted methoxy group of the trimethoxy-substituted ring was forced out of the molecular plane because of steric interactions with neighboring methoxy groups. The stabilities of the SCLs were generally correlated with the torsion angles of the para methoxy groups, where derivatives with smaller angles exhibited faster rates of crystallization. Mechanical perturbation of the SCL phases resulted in shear-induced crystallization of PH, PC1, PC3, and NC6 derivatives. In some cases, traditional mechanochromic luminescence with a crystalline-to-amorphous phase transition was also observed, which indicates that some trimethoxy-substituted β-diketones exhibit more than one type of mechanoresponsive luminescence.

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Section: ■ Introductionsupporting

confidence: 87%

Supercooled Liquid β-Diketones with Mechanoresponsive Emission

et al. 2019

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“…The methoxy-substituted dinaphthoylmethane derivative (dnmOMe) showed solvatochromism and AIE in addition to high contrast ML with rapid spontaneous recovery . Furthermore, because β-diketones, including methoxy-substituted derivatives, show large molar absorptivities and photostabilities, they have been screened and used as UV absorbing additives in sunscreens …”

Section: Introductionmentioning

confidence: 99%

“…18 Furthermore, because β-diketones, including methoxy-substituted derivatives, show large molar absorptivities and photostabilities, they have been screened and used as UV absorbing additives in sunscreens. 19 Successful integration of bdk dyes into commercial applications requires a thorough understanding of structure− property relationships and material processing parameters (e.g., temperature, thickness, and substrate). Prior reports describe the effects of alkyl chain length, 7,20 halide substitution, 21 size, 22 and even BF 2 coordination on the optical and room temperature self-healing properties of ML materials.…”

Section: ■ Introductionmentioning

confidence: 99%

Camera Method for Monitoring a Mechanochromic Luminescent β-Diketone Dye with Rapid Recovery

Butler¹,

Mathew²,

Sabat

et al. 2017

ACS Appl. Mater. Interfaces

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Mechanochromic luminescent (ML) materials, which show a change in emission due to an applied mechanical stimulus, are useful components in a variety of applications, including organic light-emitting diodes, force sensors, optical memory storage, and next-generation lighting materials. While there are many different ML active derivatives, few show room temperature self-erasing. Thin films of the methoxy substituted β-diketone, gbmOMe, initially exhibited blue (428 nm) emission; however, green (478 nm) emission was observed after smearing. The mechanically generated smeared state recovered so rapidly that characterization of its emission was difficult at room temperature using traditional luminescence techniques. Thus, a new complementary metal oxide semiconductor camera imaging method was developed and used to calculate the decay time of the mechanically generated smeared state (i.e., smeared-state decay; τ) for gbmOMe thin films. Additionally, this method was used to evaluate substrate and film thickness effects on ML recovery for glass and weighing paper films. The recovery behavior of gbmOMe was largely substrate-independent for the indicated matrixes; however, thickness effects were observed. Thus, film thickness may be the main factor in determining ML recovery behavior and must be accounted for when comparing the recovery dynamics of different ML materials. Moreover, when heated above the melting point (T = 119 °C), bulk gbmOMe powders assumed a metastable state that eventually crystallized after a few minutes at room temperature. However, melted thin films remained in an amorphous state indefinitely despite annealing at different temperatures (50-110 °C). The amorphous phase was identified as a supercooled liquid via changing the rate of cooling in differential scanning calorimetry thermograms.

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“…Thus, development of metal chelating agents would be a promising approach in protection of skin cells against UVA-induced damages. 11,12) Ethylenediaminetetraacetic acid (EDTA), a polyamino carboxylic acid, is one of the best-known and most widely used metal chelating agents in both analytical chemistry 13) and medicine. 14,15) Its usefulness results from its chemical structure, which consists of at least two carboxylate sites capable of donating electrons to the metal to which it chelates.…”

mentioning

confidence: 99%

Synthesis and Protective Effects of Bis{4-[<i>N</i>,<i>N</i>-di-(carboxymethyl)amino]phenoxy}alkane Derivatives on UVA-Induced Production of MMP-1 in Human Skin Fibroblasts

Hsu¹,

Chih-Ying

Huang

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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UV-induced matrix metalloproteinase (MMP) production is considered a cause of skin aging. In this study, a number of novel bis{4-[N,N-di-(carboxymethyl)amino]phenoxy}alkane derivatives were synthesized and evaluated as UVA-protective agents. These compounds significantly protected human dermal fibroblast (HDF) cells from UVA-induced cytotoxicity and inhibited MMP-1 activation and expression with potency comparable to desferoxamine (DFO). Promoter activity assay indicated that they inhibited MMP-1 expression at the transcriptional level. Further studies revealed that the mechanism of these compounds may include blockage of the UVA-induced activation of the p38/mitogen-activated protein kinase (MAPK) and c-Jun N-terminal kinase (JNK) pathways. Together, these results suggest that further development of these compounds may be of interest.

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Synthesis and spectroscopic examination of various substituted 1,3-dibenzoylmethane, active agents for UVA/UVB photoprotection

Cited by 9 publications

References 38 publications

Supercooled Liquid β-Diketones with Mechanoresponsive Emission

Supercooled Liquid β-Diketones with Mechanoresponsive Emission

Camera Method for Monitoring a Mechanochromic Luminescent β-Diketone Dye with Rapid Recovery

Synthesis and Protective Effects of Bis{4-[<i>N</i>,<i>N</i>-di-(carboxymethyl)amino]phenoxy}alkane Derivatives on UVA-Induced Production of MMP-1 in Human Skin Fibroblasts

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