Identifying Photoreaction Products in Cinnamate-Based Photoalignment Materials

Adams, Donat J.; Chappellet, Sabrina; Lincker, Frédéric; Ibn‐Elhaj, Mohammed; Watts, Benjamin; Iannuzzi, Marcella; Jung, Dubravka Šišak; Pignedoli, Carlo A.; Passerone, Daniele

doi:10.1021/jp504765f

Cited by 5 publications

(3 citation statements)

References 41 publications

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“…In detail, the generation of two intense bands at 1750 and 1700 cm –1 , probably associated to carbonyl groups occurring in different dimeric forms of cinnamic acid units (e.g., truxillic acid or truxinic acid units generated from head-to-tail and head-to-head monomer interactions, inset in Figure S1), is clearly visible in the spectrum of CINN after UV irradiation at 365 nm for 24 h. Moreover, a significant depletion of the CC vibration at 1630 cm –1 is detectable. These results suggest that an almost complete conversion to the dimeric forms has occurred . Subsequent UV irradiation at 254 nm leads to a very slow but progressive depletion of the bands related to the dimeric species, envisaging a gradual recovery of the initial structure.…”

Section: Results and Discussionsupporting

confidence: 80%

“…These results suggest that an almost complete conversion to the dimeric forms has occurred. 30 Subsequent UV irradiation at 254 nm leads to a very slow but progressive depletion of the bands related to the dimeric species, envisaging a gradual recovery of the initial structure.…”

Section: Results and Discussionmentioning

confidence: 99%

“…Although widely reported in the literature, 27,30 the photochemical cross-linking behavior of the re-crystallized trans-cinnamic acid was preliminary verified by ATR-FTIR and UV−vis spectroscopy. The results are summarized in Figure S1 (see Supporting Information).…”

Section: Photoreversible Properties Of Re-crystallized Cinnmentioning

confidence: 99%

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Synthesis and Characterization of Alkoxysilane-Bearing Photoreversible Cinnamic Side Groups: A Promising Building-Block for the Design of Multifunctional Silica Nanoparticles

et al. 2022

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The present study reports on the synthesis of a new alkoxysilane-bearing light-responsive cinnamyl group and its application as a surface functionalization agent for the development of SiO2 nanoparticles (NPs) with photoreversible tails. In detail, cinnamic acid (CINN) was activated with N-hydroxysuccinimide (NHS) to obtain the corresponding NHS-ester (CINN–NHS). Subsequently, the amine group of 3-aminopropyltriethoxysilane (APTES) was acylated with CINN–NHS leading to the generation of a novel organosilane, CINN-APTES, which was then exploited for decorating SiO2 NPs. The covalent bond to the silica surface was confirmed by solid state NMR, whereas thermogravimetric analysis unveiled a functionalization degree much higher compared to that achieved by a conventional double-step post-grafting procedure. In light of these intriguing results, the strategy was successfully extended to naturally occurring sepiolite fibers, widely employed as fillers in technological applications. Finally, a preliminary proof of concept of the photoreversibility of the obtained SiO2@CINN-APTES system has been carried out through UV diffuse reflectance. The overall outcomes prove the consistency and the versatility of the methodological protocol adopted, which appears promising for the design of hybrid NPs to be employed as building blocks for photoresponsive materials with the ability to change their molecular structure and subsequent properties when exposed to different light stimuli.

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Section: Results and Discussionsupporting

confidence: 80%

Section: Results and Discussionmentioning

confidence: 99%