Effects of the number and position of methoxy substituents on triphenylamine-based chalcone visible-light-absorbing photoinitiators

Yen, Shih-Chieh; Lee, Zhong-Han; Ni, Jen‐Shyang; Chen, Ching‐Chin; Chen, Yung‐Chung

doi:10.1039/d2py00604a

Cited by 12 publications

(3 citation statements)

References 57 publications

(73 reference statements)

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“…The oxidation potential of the compounds ( Figure 3 a) had the following order: NA-1 (1.64 V) > NA-2 (1.62 V) > NA-3 (1.39 V) > NA-4 (1.35 V). As expected, NA-3 and NA-4 oxidized at a relative lower oxidation potential because of the presence of an electron-donating methoxy substitution in its naphthalene unit [ 47 ]. Furthermore, the NA-1 was oxidized at the highest potential due to the presence of the 2-naphthalene accompanied by methoxy-free in its structure.…”

Section: Resultsmentioning

confidence: 59%

Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization

et al. 2022

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In order to discuss the polymerization effect from the substituted position and methoxy group of Type I photinitiators, a series of naphthalene-based oxime esters was designed and synthesized. Compared to the 2-naphthalene-substituted compound, the UV absorption region of the 1-naphthalene-based compound was greatly improved. In addition, the methoxy substitution exhibited longer absorption characteristics than did the methoxy-free one. The photochemical reaction behavior of these novel compounds was also studied by photolysis, cyclic voltammetry (CV), and electron spin resonance (ESR) experiments. Finally, the initiation abilities of naphthalene-based oxime esters toward trimethylolpropane triacrylate (TMPTA) monomer were conducted through the photo-DSC instrument under UV and a 405@nm LED lamp. Remarkedly, the naphthalene-based oxime ester (NA-3) that contains 1-naphthalene with o-methoxy substituent showed the rather red-shifted absorption region with the highest final conversion efficiency under UV (46%) and 405@nm LED (41%) lamp irradiation.

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Section: Resultsmentioning

confidence: 59%

Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization

et al. 2022

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“…Triphenylamine is particularly amenable to the majority of typical chemical reactions that form the core of Organic Chemistry. [33][34][35] A series of triphenylamine-based oxime esters were investigated by Chen and coworkers in 2020 for their potential use as visible light photoinitiators. [36] In Scheme 4, chemical structures of four different triphenylamine-based Type I photoinitiators (TP-1-TP-4) and the synthetic route to access to these structures are shown.…”

Section: Triphenylamine Based-oxime Estersmentioning

confidence: 99%

A review on recently proposed oxime ester photoinitiators

Hammoud

Hijazi

Schmitt

et al. 2023

European Polymer Journal

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“…For Type II photoinitiators systems, chalcone-based compound was classified as a promising hydrogen acceptor photoinitiator due to the facile synthetic procedures and long absorption wavelengths. [19][20][21] For further boarding the light absorption regions of the chalcone, different chromophores such as triphenylamine, [22][23][24] carbazole, [22,25] phenothiazine, [26] aromatic ring, [27,28] heterocyclic structures [29] had been introduced by the researchers. Furthermore, symmetrical bis-chalcones combine two chromophores extended conjugation length more significantly, which were beneficial for the light harvesting.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of One‐Component Type II Visible‐Light‐Absorbing Chalcones Containing Fused Aromatic Rings and Investigation of Free Radical Photopolymerization Properties

Yen,

Ni,

Chen

2024

Macro Chemistry & Physics

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This paper presents four one‐component Type II visible‐light‐absorbing chalcones (CY10‐13) that containing various fused aromatic rings as its π‐conjugated moiety, that is a 2‐naphthalene moiety for CY10, 1‐naphthalene for CY11, benzofuran for CY12 and benzothiophene for CY13. The absorption region changed significantly when introducing various fused aromatic rings. However, they all exhibited good absorption properties ranging from 300 to 450 nm that could be well‐matched under UV, 365 nm and 405 nm light irradiations. Furthermore, the structure–reactivity relationship was also studied through thermal, photochemical, electrochemical and computation properties. Finally, all the chalcones demonstrated photoinitiating ability without additive additional hydrogen donor in their systems. Both of the CY11 and CY12 based photoinitiating formulations initiated sufficiently upon UV and LED@405 nm light exposures. Furthermore, triphenylamine‐substituted chalcone analogous (CY8) was added for comparison. Although CY10‐13 compounds had lower light harvesting regions than CY8, some of those new chalcones exhibited better photoreactivity. Thus, a chalcone containing fused aromatic ring featuring straightforward synthesis as well as versatile absorption region and photoinitiating performance, has great potential in photopolymerization applications.This article is protected by copyright. All rights reserved

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Effects of the number and position of methoxy substituents on triphenylamine-based chalcone visible-light-absorbing photoinitiators

Abstract: Five visible-light-absorbing triphenylamine-based chalcone photoinitiators (CY1–CY5) that contain peripheral triphenylamines at both sides with various methoxy substituents of the triphenylamine moiety have been synthesized for application in free radical photopolymerization....

Cited by 12 publications

References 57 publications

Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization

Naphthalene-Based Oxime Esters as Type I Photoinitiators for Free Radical Photopolymerization

A review on recently proposed oxime ester photoinitiators

Synthesis of One‐Component Type II Visible‐Light‐Absorbing Chalcones Containing Fused Aromatic Rings and Investigation of Free Radical Photopolymerization Properties

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