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Scaling-up UV-mediated Intramolecular-Photo-Dehydro-Diels-Alder reactions using a Homemade High-Performance Annular Continuous-Flow Reactor
摘要： In this communication, we present a self-made annular continuous-flow reactor, which can be used in the UV/Vis-range in an internal numbering-up manner. As a model reaction, we chose a powerful and batch scale-limited benzoannelation method, which is an intramolecular Photo-Dehydro-Diels-Alder (IMPDDA) reaction. The scaling-up potential of this particular photochemical benchmark reaction towards the preparation of macrocylic (1,7)naphthalenophanes by variation of selected flow parameters is presented.
关键词： flow photochemistry,scaling-up,photocycloaddition,Photo-Dehydro-Diels-Alder reaction
更新于2025-09-23 15:21:01
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Quinoidal Oligothiophenes Having Full Benzene Annelation: Synthesis, Properties, Structures, and Acceptor Application in Organic Photovoltaics
摘要： To achieve a complete closed-shell quinoidal state, bis(dicyanomethylene)-substituted quinoidal terthiophenes bearing benzene annelation at all thiophene rings were synthesized using a retro-Diels?Alder reaction as the key step. The unique structures and properties originating from the full benzene annelation were revealed by X-ray analysis as well as property measurements. Organic solar cells based on the combination of a donor polymer with a quinoidal terthiophene as an acceptor showed a power conversion e?ciency of 1.39%.
关键词： organic photovoltaics,retro-Diels?Alder reaction,non-fullerene acceptor,quinoidal oligothiophenes,benzene annelation
更新于2025-09-12 10:27:22
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Photo-Cross-Linkable Polymer Inks for Solution-Based OLED Fabrication
摘要： We introduce a catalyst-free, highly e?cient, ambient temperature Diels?Alder reaction employing o-methylbenzaldehyde derivatives as photocaged dienes as an ideal approach for forming three-dimensional insoluble networks for inkjet printing of OLED emissive layer. Herein, poly(methyl methacrylate) based polymers containing 4-(9H-carbazol-9-yl)-2-(3′-hydroxy-[1,1′-biphenyl]-3-yl)isoindoline-1,3-dione as a blue-green (λ max = 495?500 nm) thermally activated delayed ?uorescence (TADF) emitter and a photochemically active maleimide/o-methylbenzaldehyde cross-linker couple were synthesized and their photo-cross-linking behavior was studied. Time resolved ?uorescence measurements con?rm that the TADF properties are maintained upon integration in a polymer network and HOMO/LUMO levels of the emitter species remain unchanged by the photo-cross-linking at 365 nm of the polymer chains. The network formation of the ?uorescent ?lms is evidenced by solvent resistance tests and monitored by Fourier transform infrared (FT-IR) spectroscopy as well as time of ?ight secondary ion mass spectroscopy (ToF-SIMS), showing the consumption of maleimide and o-methylbenzaldehyde groups with increasing irradiation time. The surface roughness is investigated via atomic force microscopy (AFM) and found to be unchanged by a solvent wash after the cross-linking. Furthermore, con?rmation that the polymer solution can be printed on an inkjet-printer and subsequently photo-cross-linked for multilayer OLED device fabrication is obtained.
关键词： photo-cross-linking,TADF emitter,polymer network,Diels?Alder reaction,inkjet printing,OLED
更新于2025-09-12 10:27:22
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[ACS Symposium Series] Raman Spectroscopy in the Undergraduate Curriculum Volume 1305 || Connecting Organic and Physical Chemistry Students with Raman Spectroscopy
摘要： The profile of Raman spectroscopy may be elevated in the undergraduate chemistry curriculum by intentionally tying together students’ experiences in the organic and physical chemistry laboratories. In this way the valuable role Raman spectroscopy can play in structure elucidation is highlighted. The Committee on Professional Training of the American Chemical Society includes the category of optical molecular spectroscopy (e.g., IR, UV-Vis, Raman, and fluorescence spectroscopies) as an option in the panel of instruments required for certification. To the authors’ knowledge there are no Raman spectroscopy experiments that build directly on the analysis of compounds synthesized by students in a prior course for the intended purpose of scaffolding the curriculum. This chapter highlights the roles Raman spectroscopy may play in the determination of molecular structure when used in conjunction with other, more common techniques. Indeed, direct comparison to infrared spectroscopy holds the potential to reinforce that technique and its applications while introducing the study of Raman spectra. A set of three reaction products from electrophilic aromatic substitution, Diels-Alder, and aldol condensation (this including site-specific deuteration) is explored. All of these reactions are currently part of the organic chemistry curriculum. By combining analyses performed in organic chemistry with new laboratories written for the physical chemistry laboratory the authors hope to impress upon undergraduates the value of Raman spectroscopy in a context that builds on their previous experiences with other molecular spectroscopy methods.
关键词： structure elucidation,undergraduate chemistry curriculum,electrophilic aromatic substitution,Diels-Alder reaction,Raman spectroscopy,infrared spectroscopy,deuteration,physical chemistry,aldol condensation,organic chemistry
更新于2025-09-04 15:30:14