Ozonolysis of the 2,6-divinyl derivative of a naphthalene diimide (NDI) affords a 2,6-diformyl-NDI, which can be used in Knoevenagel condensation reactions, as demonstrated by the synthesis of a 2,6-bis(2,2-dicyanovinyl)-NDI. UV-vis absorption and electrochemical data are compared to those of the parent NDI.
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http://dx.doi.org/10.1021/jo301876v | DOI Listing |
ChemSusChem
January 2025
Polish Academy of Sciences, Institute of Organic Chemistry, Kasprzaka 44/52, 01-224, Warsaw, POLAND.
We demonstrate the application of mechanochemistry in the synthesis of indolone-based photoswitches (hemiindigos, hemithioindigos, and oxindoles) via Knoevenagel condensation reactions. Utilizing ball-milling and an organic base (piperidine) acting as catalyst and solvent for liquid assisted grinding (LAG) conditions, we achieve rapid, solvent-free transformations, obtaining a set of known and previously unreported photoswitches, including highly functional amino acid-based photoswitches, multichromophoric derivatives and photoswitchable cavitands based on resorcin[4]arenes. The reaction under mechanochemical conditions gives moderate-to-high yields and is highly stereoselective leading to Z-isomers of hemiindigos and hemithioindigos and E-isomers of oxindoles.
View Article and Find Full Text PDFMacromol Rapid Commun
January 2025
State Key Laboratory of Applied Organic Chemistry (SKLAOC), Key Laboratory of Special Function Materials and Structure Design, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000, China.
Conjugated polymers have attracted extensive attention as semiconducting materials in wearable and flexible electronics. In this study, we utilize atom-economical Knoevenagel reaction to construct two conjugated polymers, PTDPP-CNTT and PFDPP-CNTT, based on dialdehyde-thiophene/furan-flanked diketopyrrolopyrrole (DPP) and 2,2'-(thieno[3,2-b]thiophene-2,5-diyl)diacetonitrile (CNTT). The resulting polymers exhibited suitable highest occupied molecular orbital/lowest unoccupied molecular orbital (HOMO/LUMO) energy levels, small bandgaps, and broad UV-vis-NIR absorptions (≈400-1000 nm), endowing them with photothermal and balanced ambipolar semiconducting properties with hole and electron mobilities over 10 cmVs.
View Article and Find Full Text PDFJ Org Chem
January 2025
Department of Chemistry, IIT Dharwad, Dharwad, Karnataka 580007, India.
The favorable redox properties of ferrocene have led to the extensive development of ferrocene-based systems for several electrochemical applications but have scarcely been explored for electrochromism. Here, we report the synthesis and electrochromic properties of novel π-conjugated ferrocene-dicyanovinylene systems (- and -). Monosubstituted (-) and disubstituted (-) compounds have been developed via Knoevenagel condensation of methyl-dicyanovinyl ferrocenes ( or ) with various aromatic aldehydes.
View Article and Find Full Text PDFMini Rev Med Chem
January 2025
Department of Chemistry, Faculty of Science, Universiti Teknologi Malaysia, Johor Bahru 81310, Johor, Malaysia.
Indole, a ubiquitous structural motif in bioactive compounds, has played a pivotal role in drug discovery. Among indole derivatives, indole-3-carboxaldehyde (I3A) has emerged as a particularly promising scaffold for the development of therapeutic agents. This review delves into the recent advancements in the chemical modification of I3A and its derivatives, highlighting their potential applications in various therapeutic areas.
View Article and Find Full Text PDFJ Fluoresc
January 2025
Post-Graduate and Research Department of Chemistry, Government Arts College (Autonomous), Coimbatore, Tamil Nadu, 641 018, India.
An efficient probe (E)-2-(benzo[d]thiazol-2-yl)-3-(9-ethyl-9 H-carbazol-3-yl)acrylonitrile (CZ-BTZ) for selective fluorescence "turn-on" response with cyanide (CN) ion sensor was developed by simple Knoevenagel condensation of 9-ethyl-9 H carbazole-3-carbaldehyde with 2-(benzo[d]thiazol-2-yl) acetonitrile. The sensing ability of probe CZ-BTZ was tested with different inorganic anions through spectrophotometric and spectrofluorimetric methods. The UV-vis and fluorescence spectral studies show the formation of a new adduct between CZ-BTZ and CN by appearing with a new absorbance band at 350 nm and "turn-on" fluorescence at 535 nm in CHCN: HO (8:2, v/v, pH 7.
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