A highly efficient waterborne photoinitiator for visible-light-induced three-dimensional printing of hydrogels

Wang, Jieping; Stanic, Sascha; Altun, Altan Alpay; Schwentenwein, Martin; Dietliker, Kurt; Jin, Lü; Stampfl, Jürgen; Baudis, Stefan; Liska, Robert; Grützmacher, Hansjörg

doi:10.1039/c7cc09313f

Cited by 83 publications

(75 citation statements)

References 35 publications

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“…These challenges limit the use of UV in biomedical applications, and therefore harmless visible light may outscore UV in biomedicine. Visible light is not only cytocompatible but also the depth of penetration increases with increasing wave length [20]. Photoinitiators are required to develop photocured hydrogels, and riboflavin (vitamin B2) represents an attractive non-toxic alternative to currently used photoinitiators such as Eosin Y, Igarcure 2959 and lithium phosphanate [21].…”

Section: Storage/loss Modulimentioning

confidence: 99%

Injectable visible light-cured glycol chitosan hydrogels with controlled release of anticancer drugs for local cancer therapy in vivo: a feasible study

Hyun

Park

Lim

et al. 2018

Artificial Cells, Nanomedicine, and Biotechnology

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Currently available chemotherapy is associated with serious side effects, and therefore novel drug delivery systems (DDSs) are required to specifically deliver anticancer drugs to targeted sites. In this study, we evaluated the feasibility of visible light-cured glycol chitosan (GC) hydrogels with controlled release of doxorubicin⋅hydrochloride (DOX⋅HCl) as local DDSs for effective cancer therapy in vivo. The storage modulus of the hydrogel precursor solutions was increased as a function of visible light irradiation time. In addition, the swelling ratio of the hydrogel irradiated for 10 s (GC/DOX) was greater than in 60 s (GC/DOX). In vitro release test showed that DOX was rapidly released in GC/DOX compared with GC/DOX due to the density of cross-linking. In vitro and in vivo tests including cell viability and measurement of tumor volume showed that the local treatment of GC/DOX yielded substantially greater antitumor effect compared with that of GC/DOX. Therefore, the visible light-cured GC hydrogel system may exhibit clinical potential as a local DDS of anticancer drugs with controlled release, by modulating cross-linking density.

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Section: Storage/loss Modulimentioning

confidence: 99%

Injectable visible light-cured glycol chitosan hydrogels with controlled release of anticancer drugs for local cancer therapy in vivo: a feasible study

Hyun

Park

Lim

et al. 2018

Artificial Cells, Nanomedicine, and Biotechnology

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“…More interestingly, the similar CQ‐based PIS (CQ/iodonium salt (i.e.,[4‐[octyloxy]phenyl]phenyliodonium hexafluoroantimonate)/EDB) was reported for the polymerization of epoxide under blue light conditions for an additive manufacturing approach (i.e., solution mask liquid lithography) . Recently, an increasing number of novel PISs have been emerging and exhibited high efficiency for free‐radical and/or cationic photopolymerization under visible light . These novel PISs are mainly synthesized with designated chemical structures.…”

Section: Introductionmentioning

confidence: 99%

1,2‐Diketones as photoinitiators of both cationic and free‐radical photopolymerization under UV (392 nm) or Blue (455 nm) LEDs

Zhang

Wang

Lalevée

et al. 2020

Journal of Polymer Science

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The photoinitiation abilities of three 1,2‐diketones [i.e., acenaphthenequinone (ANPQ), aceanthrenequinone (AATQ), and 9,10‐phenanthrenequinone (PANQ)]‐based photoinitiating systems [PISs, with additives such as iodonium salt, N‐vinylcarbazole (NVK), tertiary amine, and phenacyl bromide (R‐Br)] for cationic photopolymerization and free‐radical photopolymerization under the irradiation of ultraviolet (UV; 392 nm) or blue (455 nm) light‐emitting diode (LED) bulb are investigated. All 1,2‐diketones studied exhibit ground state absorption that match with the emission spectra of UV (392 nm) or blue LED (455 nm) better than that of the well‐known blue‐light‐sensitive photoinitiator camphorquinone (CQ). In particular, AATQ/iodonium salt/NVK can show high photoinitiating ability (with epoxide conversion yield >70%) under the UV light irradiation due to the effect of NVK. In addition, 1,2‐diketone/iodonium salt (and optional NVK) systems are capable of initiating free‐radical photopolymerization of methacrylates, with conversions of 50–58%. Furthermore, some 1,2‐diketone/tertiary amine (and optional R‐Br) combinations are found to demonstrate high efficiency to initiate free‐radical photopolymerization, and 71% of methacrylate conversion can be achieved with PANQ/tertiary amine/R‐Br PIS. Some 1,2‐ketone‐based PISs can even exhibit higher efficiency than the CQ‐based systems. The photochemical mechanism of the radical generation from the 1,2‐diketone‐based PISs is investigated and found to be consistent with the related photopolymerization efficiency. © 2020 Wiley Periodicals, Inc. J. Polym. Sci. 2020, 58, 792–802

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“…in the fields of hydrogel production, inkjet printing, cell encapsulation, and 3D printing). [14][15][16][17][18][19][20][21][22][23] Upon the photolysis of BAPOs in the presence of alcohols, time-resolved EPR spectra have been reported, and phosphorus-containingr adicals have been assigned to the EPR data (for details, see Chapter 10 in the Supporting Information). [24,25] Herein, we undertake an in-depth investigation of the reactivity of BAPO derivatives 1-3 (Scheme1)i na queous and alcoholic media.…”

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confidence: 99%

Unprecedented Bifunctional Chemistry of Bis(acyl)phosphane Oxides in Aqueous and Alcoholic Media

Schmallegger

Eibel

Menzel

et al. 2019

Chemistry A European J

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Tailor‐made photoinitiators play an important role for efficient radical polymerisations in aqueous media, especially in hydrogel manufacturing. Bis(acyl)phosphane oxides (BAPOs) are among the most active initiators. Herein, we show that they display a remarkable photochemistry in aqueous and alcoholic media: Photolysis of BAPOs in the presence of water or alcohols provides a new delocalized π‐radical, which does not participate in the polymerization. It either converts into a monoacylphosphane oxide acting as a secondary photoactive species or it works as a one‐electron reducing agent. Upon the electron‐transfer process, it again produces a dormant photoinitiator. We have established the structure and the chemistry of this π radical using steady‐state and time‐resolved (CIDEP) EPR together with ESI‐MS, NMR spectroscopy, and DFT calculations. Our results show that bis(acyl)phosphane oxides act as bifunctional reagents when applied in aqueous and alcoholic media.

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A highly efficient waterborne photoinitiator for visible-light-induced three-dimensional printing of hydrogels

Abstract: A bis(acyl)phosphane oxide (BAPO) photoinitiator was conveniently synthesized in an efficient one-pot process. It shows excellent dispersibility in water, good storage stability, and high photo-reactivity in 3D printing of hydrogels under visible-light irradiation (460 nm).

Cited by 83 publications

References 35 publications

Injectable visible light-cured glycol chitosan hydrogels with controlled release of anticancer drugs for local cancer therapy in vivo: a feasible study

Injectable visible light-cured glycol chitosan hydrogels with controlled release of anticancer drugs for local cancer therapy in vivo: a feasible study

1,2‐Diketones as photoinitiators of both cationic and free‐radical photopolymerization under UV (392 nm) or Blue (455 nm) LEDs

Unprecedented Bifunctional Chemistry of Bis(acyl)phosphane Oxides in Aqueous and Alcoholic Media

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