pi-Expanded Ketocoumarins as Efficient, Biocompatible Initiators for Two-Photon-Induced Polymerization (Articolo in rivista)

Type
Label
  • pi-Expanded Ketocoumarins as Efficient, Biocompatible Initiators for Two-Photon-Induced Polymerization (Articolo in rivista) (literal)
Anno
  • 2014-01-01T00:00:00+01:00 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#doi
  • 10.1021/cm500612w (literal)
Alternative label
  • Nazir, Rashid; Danilevicius, Paulius; Ciuciu, Adina I.; Chatzinikolaidou, Maria; Gray, David; Flamigni, Lucia; Farsari, Maria; Gryko, Daniel T. (2014)
    pi-Expanded Ketocoumarins as Efficient, Biocompatible Initiators for Two-Photon-Induced Polymerization
    in Chemistry of materials
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Nazir, Rashid; Danilevicius, Paulius; Ciuciu, Adina I.; Chatzinikolaidou, Maria; Gray, David; Flamigni, Lucia; Farsari, Maria; Gryko, Daniel T. (literal)
Pagina inizio
  • 3175 (literal)
Pagina fine
  • 3184 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 26 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#pagineTotali
  • 10 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroFascicolo
  • 10 (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • Warsaw University of Technology; Fdn Res & Technol Hellas FORTH; Consiglio Nazionale delle Ricerche (CNR); University of Crete; Polish Academy of Science (literal)
Titolo
  • pi-Expanded Ketocoumarins as Efficient, Biocompatible Initiators for Two-Photon-Induced Polymerization (literal)
Abstract
  • A series of pi-expanded coumarins comprising of 4-5 conjugated rings were designed and synthesized. The strategic placement of two dialkylamino groups containing long alkyl chains attached to the peripheral ends of bis-coumarins resulted in dyes with superb solubility. As alpha,beta-unsaturated ketones, these compounds display properties of donor-acceptor-donor (D-A-D)-type chromophores. Photophysical studies of the new functional dyes revealed a combination of favorable properties: strong absorption of blue and green light, weak fluorescence, reasonable two-photon absorption (2PA) cross-section, and complete solubility in nonpolar solvents. The fluorescence lifetimes of coumarin-derived alpha,beta-unsaturated ketones were measured for the first time. The placement of two amine groups at peripheral positions of the dyes produced two-photon absorption cross-section values at the level of 150-400 GM around 800 nm, which generated two-photon photoinitiation. The highest 2PA cross-section was approximately 400 GM for the derivative of 4-methylcyclohexanone. Directly using these compounds as sensitizer or initiator, two (2D)- and three-dimensional (3D) nanopatterns were successfully fabricated by two-photon initiated polymerization. 3,3'-Carbonyl-biscoumarin, which contains two dihexylamino substituents at positions 7 and 7' possesses the largest fabrication window. MC3T3-E1 preosteoblastic cells exhibited strong adherence to all pi-expanded coumarins and the same spindle-shaped morphology as the tissue culture treated polystyrene control surface. Additionally, our results showed an increase in cell proliferation after 3 and 7 days in culture, as well as a high cell viability of approximately 100% on all materials compared to the control surface. These findings confirm that D-A-D-type ketocoumarin derivatives used as potential photoinitiators are noncytotcodc and can be used in the fabrication of biomaterial scaffolds for tissue engineering applications. (literal)
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