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Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators.

ABSTRACT: Three novel visible-light absorbing benzophenone-based hydrogen acceptors (BPD-D, BPDM-D and BPDP-D) were designed on the basis of a donor-benzophenone-donor structural backbone. Mono or diketone units and double diphenylamine electron-donating groups in para-or meta-positions were introduced to comprehend the electronic and structural effects on free radical photopolymerization (FRPP). Such a structural change leads not only to a red-shift of the absorption maxima but strongly enhances their molar extinction coefficients compared to the commercial phototinitiators such as benzophenone (BP) and 4,4'-bis(diethylamino) benzophenone (EMK). In addition, excellent melting points and thermal decomposition temperatures were achieved for those novel compounds. Further, the photochemical reaction behavior was studied by cyclic voltammograms (CV), photolysis and electron spin resonance (ESR) spectroscopy. Finally, benzophenone derivatives in combination with an amine (TEA, triethylamine) as a co-initiator were prepared and initiated the FRPP of trimethylolpropane trimethacrylate (TMPTMA) using a UV lamp as a light source. When used in stoichiometric amounts, the BPDP-D/TEA had the best double bond conversion efficiency among all the compounds studied, and were even superior to the reference compounds of BP/TEA and EMK/TEA. The results and conclusions could provide the fundamental rules applicable for the structural design of benzophenone derivative-based photoinitiators.

SUBMITTER: Huang TL

PROVIDER: S-EPMC8199044 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Project description:Photopolymerized biomimetic hydrogels with adaptable properties have been widely used for cell and tissue engineering applications. As a widely adopted gel cross-linking method, photopolymerization provides experimenters on-demand and spatial-temporal controls in gelation kinetics. Long wavelength ultraviolet (UV) light initiated photopolymerization is among the most popular methods in the fabrication of cell-laden hydrogels owing to its rapid and relatively mild gelation conditions. The use of UV light, however, still causes concerns regarding its potential negative impacts on cells. Alternatively, visible light based photopolymerization can be used to cross-link cell-laden hydrogels. The majority of visible light based gelation schemes involve photoinitiator, co-initiator, and comonomer. This multicomponent initiation system creates added challenges for optimizing hydrogel formulations. Here, we report a co-initiator/comonomer-free visible light initiated thiol-norbornene photopolymerization scheme to prepare modular biomimetic hydrogels suitable for in situ cell encapsulation. Eosin-Y was used as the sole initiator to initiate modular gelation between synthetic macromers (e.g., thiolated poly(vinyl alcohol) or poly(ethylene glycol)) and functionalized extracellular matrices (ECMs) including norbornene-functionalized gelatin (GelNB) or thiolated hyaluronic acid (THA). These components are modularly cross-linked to afford bioinert (i.e., purely synthetic), bioactive (i.e., using gelatin), and biomimetic (i.e., using gelatin and hyaluronic acid) hydrogels. The stiffness of the hydrogels can be easily tuned without affecting the contents of the bioactive components. Furthermore, the use of naturally derived biomacromolecules (e.g., gelatin and HA) renders these hydrogels susceptible to enzyme-mediated degradation. In addition to demonstrating efficient and tunable visible light mediated gelation, we also utilized this biomimetic modular gelation system to formulate artificial tumor niche and to study the effects of cell density and gel modulus on the formation of pancreatic ductal adenocarcinoma (PDAC) spheroids.

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Ketone Number and Substitution Effect of Benzophenone Derivatives on the Free Radical Photopolymerization of Visible-Light Type-II Photoinitiators.

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