The development of high-performance n-type polymer semiconductors is powered by the design and synthesis of electron-deficient building blocks with optimized physicochemical properties. By meticulously installing an imide group onto fluorene and its cyanated derivative, we report here two very electron-deficient building blocks, imide-functionalized fluorenone (FOI) and its cyanated derivative (FCNI), both featuring a deep-lying lowest unoccupied molecular orbital energy level down to -4.05 eV and highly coplanar framework, endowing them ideal units for constructing n-type polymers. Thus, a series of polymers are built from them, exhibiting unipolar n-type transport character with a highest electron mobility of 0.11 cm V s . Hence, FOI and FCNI offer a remarkable platform for accessing high-performance n-type polymers and the imide functionalization of appropriate (hetero)arenes is a powerful strategy for developing polymers with deep-lying LUMOs for n-type organic electronics.
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http://dx.doi.org/10.1002/anie.202205315 | DOI Listing |
Org Lett
January 2025
School of Chemistry, Indian Institute of Science Education and Research Thiruvananthapuram, Thiruvananthapuram 695551, Kerala, India.
Herein, we report a formal C-C bond azidation and cyanation of unactivated aliphatic ketones using commercially available tosyl azide and cyanide, respectively. A visible-light-mediated organophotocatalyst enables radical azidation and cyanation of ketone-derived pro-aromatic dihydroquinazolinones (under mostly redox-neutral conditions) as supported by preliminary mechanistic studies. These metal-free and scalable protocols can be used to synthesize tertiary, secondary, and primary alkyl azides and nitriles with good functional group tolerance and postsynthetic diversification of the azide group, including bioconjugation.
View Article and Find Full Text PDFNeurotoxicology
December 2024
Université Catholique de Bukavu (UCB), Center for Tropical Diseases and Global Health (CTDGH), Bukavu, Democratic Republic Congo; University of Fribourg, Faculty of Science and Medicine, Department of Neuroscience and Movement Science, Fribourg, Switzerland.
Introduction: Chronic cassava-derived cyanide poisoning is associated with the appearance of konzo, a tropical spastic paraparesis due to selective upper motor neuron damage. Whether the disease is caused by a direct action of cyanide or its metabolites is still an open question. This preliminary study assessed the neurotoxic effects of thiocyanate (SCN) and cyanate (OCN), two cyanide metabolites hypothesized to be plausible toxic agents in konzo.
View Article and Find Full Text PDFJ Agric Food Chem
December 2024
College of Food Science and Engineering, Hubei Key Laboratory for Processing and Transformation of Agricultural Products, Wuhan Polytechnic University, Wuhan, Hubei 430023, China.
J Am Chem Soc
November 2024
Department of Chemistry, The University of Manchester, Oxford Road, Manchester M13 9PL, U.K.
Stereoselective alkene 1,2-difunctionalization is a privileged strategy to access three-dimensional C(sp)-rich chiral molecules from readily available "flat" carbon feedstocks. State-of-the-art approaches exploit chiral transition metal-catalysts to enable high levels of regio- and stereocontrol. However, this is often achieved at the expense of a limited alkene scope and reduced generality.
View Article and Find Full Text PDFChem Asian J
January 2025
SupraSelen Laboratory, Department of Organic Chemistry, Institute of Chemistry, Universidade Federal Fluminense, Campus do Valonguinho, Niterói, RJ, 24020-141, Brazil.
A novel strategy to catalyze alkylation reactions through chalcogen bond interaction using a supramolecular structure is presented herein. Utilizing just 1.0 mol % of selenoxide-pillar[5]arene (P[5]SeO) as the catalyst we achieved efficient catalysis in the cyanation of benzyl bromide in water.
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