A solid supported procedure for the synthesis of benzoxazinones, dihydropyrazinones, quinoxalinones, and dihydrooxazinones using immobilized oxazolones in combination with difunctional nucleophiles as cleavage agent is presented. The scope of the novel method has been demonstrated through subsequent modification of the parent oxazolone scaffold on solid supports using conversions with electrophiles or CuAAC reactions to give functionalized pyrazin-2-ones. The described method allows the synthesis of the target heterocycles in good yields via three to five steps on solid phases with only one chromatographic purification step.
Molecular machines and responsive materials open a plethora of new opportunities in nanotechnology. We present an oriented crystalline array of diarylethene (DAE)‐based photoactuators, arranged in a way to yield an anisotropic response. The DAE units are assembled, together with a secondary linker, into a monolithic surface‐mounted metal–organic framework (SURMOF) film. By Infrared (IR) and UV/Vis spectroscopy as well as by synchrotron X‐ray diffraction, we show that the light‐induced extension changes of the molecular DAE linkers multiply to yield mesoscopic and anisotropic length changes. Due to the special architecture and substrate‐bonding of the SURMOF, these length changes are transferred to the macroscopic scale, leading to the bending of a cantilever and performing work. This research shows the potential of assembling light‐powered molecules into SURMOFs to yield photoactuators with a directed response, presenting a path to advanced actuators.
Data management in universities is a challenging endeavor in particular due to the diverse infrastructure of devices and software in combination with limited budget. Nevertheless, in particular the analytical measurements and data sets need to be stored if possible digitally and in a well-organized manner. This manuscript describes how scientists can achieve a data management workflow focusing on data capture and storage by small adaptions to commonly used systems. The presented method includes data transfer options from ubiquitous devices like NMR instruments, GC (MS) or LC (MS), IR and Raman, or mass spectrometers to a central server and the visualization of the available data files in an electronic lab notebook (ELN). The given instruments were chosen according to the needs of synthetic chemists, in particular devices needed in organic, inorganic and polymer chemistry where single data files in the range of several megabytes per data set are produced. Altogether, three different data transfer systems were elaborated to allow a flexible handling of different devices running with different proprietary software: The first procedure allows data capture via the use of a mail server as data exchange point. With the second procedure, data are automatically mirrored from a local file folder to a central storage server where new files are monitored and processed. The third procedure was designed to transfer data with manual support to a central server which is supervised to register new information. All components that are necessary to install and use the herein elaborated functions are available as Open Source and the designed workflows are described step by step to facilitate the adaption of procedures in other universities accordingly if desired.
Modular synthesis of structurally diverse functionalized azobiphenyls and azoterphenyls for the realization of optically switchable materials has been described. The corresponding synthesis of azobiphenyls and azoterphenyls by stepwise Mills/Suzuki‐Miyaura cross‐coupling reaction, proceeds with high yields and provides facile access to a library of functionalized building blocks. The synthetic methods described herein allow combining several distinct functional groups within a single unit, each intended for a specific task, such as 1) the −N=N− azobenzene core as a photoswitchable moiety, 2) aryls and heteroaryls, functionalized with carboxylic acids or pyridine at its peripheries, as coordinating moieties and 3) varying substitution, size and length of the backbone for adaptability to specific applications. These specifically designed azobiphenyls and azoterphenyls provide modular bricks, potentially useful for the assembly of a variety of polymers, molecular containers and coordination networks, offering a high degree of molecular functionality. Once integrated into materials, the azobenzene system, as a side group on the organic linker backbone, can be exploited for remotely controlling the structural, mechanical or physical properties, thus being applicable for a broad variety of ‘smart’ applications.
Photocatalysis for organic synthesis has experienced rapid progress over the last decades, which serves as an alternative to conventional synthetic routines. However, the photochemical reactor setup of many published works remains ambiguous due to missing standardized protocols. Therefore, a general design of batch photoreactor is required to circumvent the problem of difficult reproducibility and experimental inconsistencies. In this report which we have termed a technical note, a novel batch photoreactor with temperature feedback control and modulated light intensity was assembled from several low-cost, commercially available components, which will assist other researchers to reproduce this standardized reactor for use in their own research.
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