Efficient Synthesis of Chromone and Flavonoid Derivatives with Diverse Heterocyclic Units

Chromones and flavonoids are important bioactive compounds. We envisioned that new heterocyclic‐substituted chromones or flavonoids might act as new bioactive compounds. To obtain diverse molecules, we developed an efficient one‐pot synthesis by Michael aldol reaction of chromone and flavonoid derivatives bearing heterocyclic units. The 2,3‐heterocyclic‐substituted chromones were obtained in one step. Moreover, the use of substituted benzaldehydes and subsequent addition of heterocyclic aldehydes gave 3‐pyridyl‐substituted flavones. We also examined these one‐pot reactions in the solid phase. To introduce an additional point of diversity into the molecules, Suzuki–Miyaura coupling was performed. Furthermore, we identified the cytotoxicity of the synthesized compounds against cancer cells (PANC1 and HeLa cells). Several compounds were cytotoxic to these cancer cells.     

Switching phenomenon induced by breakdown of chaotic phase synchronization

We investigate chaotic phase synchronization (CPS) in three-coupled chaotic oscillator systems. According to the coupling strength and mismatches in the frequencies of these oscillators, we can observe complete CPS where all three oscillators exhibit CPS, and partial CPS where only two oscillators exhibit CPS. When the coupling strength is weakened, we observe a phenomenon that complete CPS among the three oscillators is suddenly disrupted without going through partial CPS. In this case oscillators exhibit quasi-CPS where two oscillators appear to exhibit CPS transiently, and the combination of the two oscillators changes with time. We call this phenomenon CPS switching D. It is revealed that phase fluctuation plays an important role in CPS switching D. It is also shown that the amplitude with a specific structure strengthens the degree of CPS switching. In the present paper, we characterize this CPS switching and discuss its mechanism.     

Sequential Chiral Induction and Regulator-Assisted Chiral Memory of Pillar[5]arenes

Chirality transfer is widely observed in life processes, and many artificial chiral transfer systems have been developed. In these systems, chiral information is transferred from chiral inducers to chiral acceptors by a direct chiral induction process and a direct chiral memorization process. We have developed ternary nondirect chiral transfer systems based on pillar[5]arenes, in which a third factor was introduced as a regulator. The planar chirality of an acceptor was induced and memorized by a chiral inducer with precise control by a regulator. In the chiral induction period, the feed sequence of the chiral inducer and regulator affected the chiral induction behavior of the chiral acceptor. The chiral memory ability of the acceptor was substantially improved by the combined action of the chiral inducer and regulator.     

Propagation of two longitudinal waves in a cancellous bone with the closed pore boundary

Ultrasound propagation in cancellous bone (porous media) under the condition of closed pore boundaries was investigated. A cancellous bone and two plate-like cortical bones obtained from a racehorse were prepared. A water-immersion ultrasound technique in the MHz range and a three-dimensional elastic finite-difference time-domain (FDTD) method were used to investigate the waves. The experiments and simulations showed a clear separation of the incident longitudinal wave into fast and slow waves. The findings advance the evaluation of bones based on the two-wave phenomenon for in vivo assessment.     

Carbon monoxide oxidation at room temperature on Pt/CeO2-ZrO2-Bi2O3 catalysts

A novel Pt/CeO(2)-ZrO(2)-Bi(2)O(3) catalyst was prepared to realize complete CO oxidation at room temperature or below even in the presence of moisture. Using this catalyst, a high CO oxidation activity and a high stability against moisture have been realized simultaneously.     

Shift-multiplexed holographic digital data page storage in a nanoparticle-(thiol-ene) polymer composite film

We demonstrate shift-multiplexed holographic storage of 180 digital data pages with low symbol-error rates in a thick (250 μm) SiO2 nanoparticle-polymer composite film using step-growth thiol-ene photopolymerization. A two-dimensional 2:4 modulation code was employed for formatting digital data pages in order to reduce the average intensity of code block without decreasing the coding efficiency. This study clearly shows the feasibility of the thiol-ene based nanoparticle-polymer composite system as a holographic data storage medium.     

Parity Projected QCD Sum Rule of the Nucleon with MEM

The nucleon and its negative-parity excited states are examined in a maximum entropy method analysis of QCD sum rules. We derive the parity projected nucleon sum rules with all known first order α _s corrections to the Wilson coefficients of the operator product expansion (OPE). As these corrections have turned out to be large, we suppress them by using a phase-rotated Gaussian kernel. This phase rotation strongly suppresses the continuum contribution and improves the convergence of the OPE. The resulting sum rule has the interesting feature that it is dominated by the term containing the chiral condensate of dimension 3. Analyzing this sum rule by the maximum entropy method, we are able to extract information of both the positive and negative parity states.     

Surface-induced enantiomorphic crystallization of achiral fullerene derivatives in thin films

The chirality of organic semiconductors is important for various applications in optoelectronics and spintronics. Here, we propose a new strategy to induce structural chirality in achiral organic semiconductors in thin films. Enantiomeric fullerene derivatives (S)-pSi and (R)-pSi, which have oligo(dimethylsiloxane) as a low-surface-energy moiety, were synthesized and used as surface-segregated monolayers (SSMs) in spin-coated films of several achiral fullerene derivatives. Upon thermal annealing, the presence of the chiral SSMs led to the crystallization of the fullerenes in the films as an SSM-induced crystal phase at lower temperatures. The crystallized films showed circular dichroism ascribed to the fullerene absorption, the sign and the intensity of which depended on the handedness of the SSM molecules and the film thickness, respectively. These results indicate that the achiral fullerene derivatives in the films were induced by the SSMs to crystallize into enantiomorphic crystals. Our approach to inducing chirality in organic thin films is compatible with many device applications.

Chiral induction: surface-segregated monolayers of chiral molecules induce the enantiomorphic crystallization of achiral fullerene derivatives in thin films.     

Heat-resistant polymers containing bipyridyl units. I. Polyimides

Polyimides containing bipyridyl units were synthesized. The bipyridyl units were successfully incorporated by polymerization of various bipyridyl diamines with aromatic tetracarboxylic acid dianhydrides. The resulting polyamic acids had inherent viscosities in the range 0.07 to 2.26, and they were converted to the polyimides by thermal cyclization. The polyimides containing the bipyridyl units exhibited varying degrees of solubility in dimethylacetamide and m-cresol and were found to be very soluble in dichloroacetic acid.     

Highly stereo- and regioselective ni-catalyzed homoallylation of aldimines with conjugated dienes promoted by diethylzinc

Under the nickel catalysis, in one pot, diethylzinc serves as a reducing agent to connect the three components of 1,3-dienes, alkyl or aryl aldehydes, and anilines to furnish 3-substituted 3,5-syn-5-(arylamino)pent-1-enes 1, the homoallylation products of aldimines with dienes, in excellent yields and with high regio- and stereoselectivity.