Two new push-pull chromophores based on triphenylamine as donor and 2-carboxymethyl-2-cyanomethylenethiazole as acceptor have been synthesized. Both exhibit strong light absorption covering from 300 to 800 nm. Electrochemical studies show HOMO-LUMO gaps of 2.01 and 1.54 eV, making, together with the panchromatic absorption, these systems promising materials in the field of molecular photovoltaic devices.
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http://dx.doi.org/10.1021/ol202242j | DOI Listing |
J Org Chem
January 2025
Department of Materials Science and Engineering, Institute of Science Tokyo, 2-12-1 Ookayama, Meguro-ku, Tokyo 152-8552, Japan.
A series of 1,1,4,4-tetracyanobuta-1,3-diene (TCBD) derivatives with various heterocyclic moieties, including pyridine, carbazole, indole, and benzothiadiazole, was newly synthesized through a [2 + 2] cycloaddition-retroelectrocyclization reaction. Symmetric electron-rich 1,3-butadiynes with end-capped heterocyclic substituents were reacted with tetracyanoethylene (TCNE), yielding the target TCBD products in 60-80% yields under ambient or mild heating conditions. The thermal stability and optical and electrochemical properties of both 1,3-butadiyne precursors and the corresponding TCBD derivatives were investigated by using thermogravimetric analysis (TGA), UV-vis spectroscopy, and cyclic voltammetry (CV).
View Article and Find Full Text PDFDalton Trans
January 2025
Institute of Chemistry, Faculty of Science and Technology, University of Silesia, Szkolna 9, 40-006 Katowice, Poland.
Over the last five decades, diimine rhenium(I) tricarbonyl complexes have been extensively investigated due to their remarkable and widely tuned photophysical properties. These systems are regarded as attractive targets for design functional luminescent materials and performing fundamental studies of photoinduced processes in transition metal complexes. This review summarizes the latest developments concerning Re(I) tricarbonyl complexes bearing donor-acceptor (D-A) and donor-π-acceptor (D-π-A) ligands.
View Article and Find Full Text PDFInorg Chem
January 2025
Institute of Chemistry, University of Silesia, Szkolna 9, 40-006 Katowice, Poland.
This paper provides extensive studies of [IrCl(Ph-py)(morph-CH-terpy-κN)]PF (), [Ir(Ph-py)(morph-CH-terpy-κN)]PF (), [IrCl(Ph-py)(Ph-terpy-κN)]PF (), and [Ir(Ph-py)(Ph-terpy-κN)]PF () designed to demonstrate the possibility of controlling the photophysical properties of mono- and bis-cyclometalated complexes [IrCl(Ph-py)(R-CH-terpy-κN)]PF and [Ir(Ph-py)(R-CH-terpy-κN)]PF through a remote electron-donating substituent introduced into the 4'-position of 2,2':6',2″-terpyridine (terpy) via the phenyl linker. The attachment of the morpholinyl (morph) group was evidenced to induce dramatic changes in the emission characteristics of the monocyclometalated Ir(III) systems with coordinated R-CH-terpy ligand (κN). In solution, the obtained complex [IrCl(Ph-py)(morph-CH-terpy-κN)]PF was found to be a rare example of dual-emissive Ir(III) systems.
View Article and Find Full Text PDFChem Asian J
November 2024
Department of Materials Science and Engineering, Tokyo Institute of Technology, 2-12-1 Ookayama, Meguro-ku, Tokyo, 152-8552, Japan.
A π-extended cyclobutenofullerene containing an N,N-dimethylanilinoethynyl group was synthesized via a one-pot cascade reaction of C with the corresponding propargylic phosphate. The cyclobutenofullerene was further modified using either one-pot or sequential post-functionalization methods, yielding derivatives containing altered addend structures. During one-pot post-functionalization, hydration reaction of the alkyne moiety continued after the formation of cyclobutenofullerenes.
View Article and Find Full Text PDFChempluschem
November 2024
Department of Chemistry, City University of Hong Kong, Hong Kong SAR, China.
The research and development of push-pull tetraene chromophores (PPT-phores) have contributed greatly to the field of organic electro-optic (EO) materials and devices since the inauguration of CLD-1 in 2001. This study is thus a systematic contribution to synthesize and characterize a series of centro-arylated PPT-phores based on strong electron-donating tetrahydroquinolinyl groups and variable strong electron-accepting tricyanofuran derivatives. In particular, we report the crystallographic data to show various packing modes of these PPT-phores with detailed information about bond length alternation and intermolecular interactions, the optical absorption edges of guest-host polymers by the Tauc model, and the anisotropy and dispersion of Pockels tensors for the poled polymers by attenuated total reflection spectroscopy.
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