Bridging pyrrole and selenophene chemistries: Molecular assemblies have been developed that allow scrutiny of the electronic communication between pyrrole and selenophene nuclei. Divergent syntheses of 2-(selenophen-2-yl)pyrroles and their N-vinyl derivatives from available 2-acylselenophenes and acetylenes in a one-pot procedure have been devised (see scheme), which provide access to these exotic heterocyclic ensembles.The divergent syntheses of 2-(selenophen-2-yl)pyrroles and their N-vinyl derivatives from available 2-acylselenophenes and acetylenes in a one-pot procedure make these exotic heterocyclic ensembles accessible. Now we face a potentially vast area for exploration with a great diversity of far-reaching consequences including conducting electrochromic polymers with repeating of pyrrole and selenophene units (emerging rivalry for polypyrroles and polyselenophenes), the synthesis of functionalized pyrrole-selenophene assembles for advanced materials, biochemistry and medicine, exciting models for theory of polymer conductivity.
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http://dx.doi.org/10.1002/chem.200900348 | DOI Listing |
Macromol Rapid Commun
October 2024
Department of Chemistry, Middle East Technical University, Ankara, 06800, Turkey.
In this study, six different donor-π-acceptor-π-donor-acceptor type random co-polymers containing benzodithiophene as a donor, benzooxadiazole (BO), and thieno[3,4-c]pyrrole-4,6-dione (TPD) as acceptor, have been synthesized and characterized. In addition to the acceptor core ratio at different values, the effect of aromatic bridge structures on the optical, electronic, and photovoltaic properties of six different random co-polymers is investigated by using thiophene and selenophene structures as aromatic bridge units. To investigate how the acceptor unit ratio and replacement of aromatic bridge units impact the structural, electronic, and optical properties of the polymers, density functional theory (DFT) calculations are carried out for the tetramer models.
View Article and Find Full Text PDFJ Mol Graph Model
June 2024
Chemistry Department, College of Science, King Khalid University (KKU), Abha 61413, P.O. Box 9004, Saudi Arabia. Electronic address:
With the goal of developing a high-performance organic solar cell, nine molecules of A-D-A-D-A type are originated in the current investigation. The optoelectronic properties of all the proposed compounds are examined by employing the DFT approach and the B3LYP functional with a 6-31G (d, p) basis set. By substituting the terminal moieties of reference molecule with newly proposed acceptor groups, several optoelectronic and photovoltaic characteristics of OSCs have been studied, which are improved to a significant level when compared with reference molecule, i.
View Article and Find Full Text PDFOrg Biomol Chem
March 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai 400076, India.
Stable nonaromatic core-modified -benzicalixhexaphyrins containing one -phenylene ring, four pyrrole rings and one heterocyclic ring such as furan, thiophene, selenophene and telluorophene connected four -sp carbons and two -sp carbons in a macrocyclic framework were synthesized. The -benzitripyrrane dicarbinol was condensed with 16-heterocycle tripyrranes under mild acid-catalyzed and inert conditions followed by open-air oxidation with DDQ to obtain macrocycles in 2-5% yields. The presence of two -OH groups in the -orientation at two different -sp carbons, which are adjacent to the -phenylene ring of the macrocycle, was confirmed through detailed 1D and 2D NMR studies.
View Article and Find Full Text PDFChem Asian J
January 2024
Department of Chemistry, Indian Institute of Technology Bombay, Powai, Mumbai, 400076, India .
A series of phenothiazine embedded heteroporphyrins containing one phenothiazine unit, two pyrrole rings and one heterocycle such as furan, thiophene, selenophene and tellurophene connected via four meso carbons were synthesized. The macrocycles were synthesized by condensing the phenothiazine based tripyrrane with corresponding 2,5-bis(hydroxymethyl)heterocycle under BF ⋅ OEt catalyzed conditions and compared the structural, spectral, and electrochemical properties with the reported phenothiazinophyrins. The studies showed that the phenothiazine embedded heteroporphyrins were nonaromatic and electronic properties were significantly altered by replacing the pyrrole ring from phenothiazinophyrin with different heterocycles.
View Article and Find Full Text PDFBiosensors (Basel)
June 2023
Faculty of Engineering, Department of Biomedical Engineering, Necmettin Erbakan University, Konya 42090, Turkey.
The molecular engineering of conjugated systems has proven to be an effective method for understanding structure-property relationships toward the advancement of optoelectronic properties and biosensing characteristics. Herein, a series of three thieno[3,4-]pyrrole-4,6-dione (TPD)-based conjugated monomers, modified with electron-rich selenophene, 3,4-ethylenedioxythiophene (EDOT), or both building blocks (, , and ), were synthesized using Stille cross-coupling and electrochemically polymerized, and their electrochromic properties and applications in a glucose biosensing platform were explored. The influence of structural modification on electrochemical, electronic, optical, and biosensing properties was systematically investigated.
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