Effect of Bridging Position on the Two-Photon Polymerization Initiating Efficiencies of Novel Coumarin/Benzylidene Cyclopentanone Dyes
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One- and two-photon photophysical and photochemical properties of dyes 3-DAC and 4-DAC containing coumarin and benzylidene cyclopentanone moieties were studied. Their ground state configurations were optimized using both Hartree-Fock and density functional theory (B3LYP functional) methods, and excited-state properties were calculated using time-dependent density functional theory. These two dyes share the same formula and possess similar structures, except for different bridging positions between the benzylidene cyclopentanone and coumarin moieties. The bridging position was found to have a significant effect on the electronic structure and photophysical and photochemical properties of the dyes. 3-DAC shows higher conjugation and is more planar than 4-DAC, and it exhibits a larger TPA cross section. In contrast, 4-DAC has a twisted conformation, exhibits a lower electron transfer free energy with initiator and shows higher sensitizing efficiencies in one-photon polymerization. Furthermore, the application potential of 3-DAC and 4-DAC in two-photon polymerization (TPP) was studied. Both dyes could be used directly as initiators in TPP. The TPP threshold energies of the corresponding resins were as low as the best reported results. High-resolution 2D and 3D nanopatterns containing low amounts of small molecule residue were successfully fabricated by TPP, demonstrating the extensive application prospects of these dyes in the fabrication of micromachines, microsensor arrays and biomedical devices.Keywords:
Cyclopentanone
Cyclopentanone
Dimethyl ether
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δ-Decalactone,an important intermediate compound for perfumes and pharmaceuticals,was synthesized with cyclopentanone and N-valeraldehyde as starting material in this paper.α-Pentylidene cyclopentanone was firstly obtained through aldol condensation and dehydration with yield of 85.0%.And then α-pentenyl cyclopentanone was prepared from α-pentylidene cyclopentanone by hydrogenation method with yield of 95.0%.Through Baeyer-Villiger oxidation,δ-decalactone was synthesized by α-pentenyl cyclopentanone and hydrogen peroxide with yield of 63.4%.And the total yield for the product was determined as 51.2% with a purity of 98.6%(GC).Some rational technological parameters,related reaction mechanisms and reaction conditions were discussed.The structure and composition of the product were characterized by IR,1HNMR and GC-MS.
Cyclopentanone
Aldol condensation
Baeyer–Villiger oxidation
Aldol reaction
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Cyclopentanone
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Abstract The asymmetric synthesis of an intermediate which enables the asymmetric syntheses of (I) and (II) is also presented.
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Cyclopentanone
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δ-decalactone,which is an important intermediate compound for perfumes and pharmaceuticals,were synthesized in this paper.A synthesis of 2-pentylidene cyclopentanone starting from cyclopentanone and n- valeraldehyde through aldol condensation,followed by dehydration,was studied,and the yield reached 85.0%.2- Pentenyl cyclopentanone was prepared in a yield of 95.0% from 2-pentylidene cyclopentanone with a hydrogenation methodology.Through Baeyer-villiger oxidation,δ-decalactone was synthesized in a yield of 63.4% from 2-pentenyi cyclopentanone with hydrogen peroxide.And the total yield for product was improved to 51.6.0% with a purity of 98.6% (GC).Some rational technological parameters,related reaction mechanisms and reaction conditions were discussed.The structures and compositions of these compounds were accomplished by IR,1H-NMR and GS-MS.
Cyclopentanone
Aldol condensation
Baeyer–Villiger oxidation
Aldol reaction
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Abstract Cyclopentanone reacts with arylidenemalononitriles 1a–c to give dihydro‐4,6‐indenedicarbonitriles 5a–c . Similarly, the diethyl dihydro‐4,6‐indenedicarboxylate derivative 6 is formed when treating ethyl α‐cyanocinnamate ( 1d ) with cyclopentanone. Cyclopenta[ b ]pyrans 5a–c are obtained from the reaction of diarylidene derivatives of cyclopentanone with malononitrile.
Cyclopentanone
Derivative (finance)
Reaction conditions
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Abstract 2, 5‐Diacetyl‐1‐cyclopentanone and 2, 5‐dibenzoyl‐1‐cyclopentanone are obtained by base induced cyclisations of ethyl 2‐acetyl‐6‐oxo‐heptanoate and ethyl 2, 5‐dibenzoyl‐pentanoate. Competing with this condensation aldol type cyclisations occur.
Cyclopentanone
Aldol condensation
Diacetyl
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