Synthesis of styryl-substituted 2-phenyl- and 1,2-diphenylcyclopenta[b]-chromenes

Porshnev, Yu. N.; Churkina, V. A.; Титов, В. В.

doi:10.1007/bf00469943

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“…The desired products have mostly been realized by classical Wittig or Horner–Wadsworth–Emmons (HWE) reaction of noncommercial Wittig or HWE salts with corresponding aldehydes under strong alkaline conditions. A subsequent isomerization reaction with traces of iodine is generally required to convert undesired cis isomer to the desired trans product . Another method to make double-bond bridges is the Heck coupling reaction, a palladium-catalyzed reaction of aryl halides with terminal alkenes .…”

Section: Introductionmentioning

confidence: 99%

“…A subsequent isomerization reaction with traces of iodine is generally required to convert undesired cis isomer to the desired trans product. 19 Another method to make double-bond bridges is the Heck coupling reaction, a palladium-catalyzed reaction of aryl halides with terminal alkenes. 20 The main drawbacks of Heck coupling are the high price of palladium catalysts and difficulties associated with catalyst recycling.…”

Section: ■ Introductionmentioning

confidence: 99%

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A Straightforward Synthesis and Structure–Activity Relationship of Highly Efficient Initiators for Two-Photon Polymerization

et al. 2013

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The development of practical two-photon absorption photoinitiators (TPA PIs) has been slow due to their complicated syntheses often reliant on expensive catalysts. These shortcomings have been a critical obstruction for further advances in the promising field of two-photon-induced photopolymerization (TPIP) technology. This paper describes a series of linear and cyclic benzylidene ketone-based two-photon initiators containing double bonds and dialkylamino groups synthesized in one step via classical aldol condensation reactions. Systematic investigations of structure–activity relationships were conducted via quantum-chemical calculations and experimental tests. These results showed that the size of the central ring significantly affected the excited state energetics and emission quantum yields as well as the two-photon initiation efficiency. In the TPIP tests the 4-methylcyclohexanone-based initiator displayed much broader ideal processing windows than its counterparts with a central five-membered ring and previously described highly active TPA PIs. Surprisingly, a writing speed as high as 80 mm/s was obtained for the microfabrication of complex 3D structures employing acrylate-based formulations. These highly active TPA PIs also exhibit excellent thermal stability and remain inert to one-photon excitation. Straightforward synthesis combined with high TPA initiation efficiency makes these novel initiators promising candidates for commercialization

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Section: Introductionmentioning

confidence: 99%

Section: ■ Introductionmentioning

confidence: 99%