Quinoidal oligothiophenes: towards biradical ground-state species

Chemistry : a European Journal
Rocío Ponce OrtizTetsuo Otsubo

Abstract

A family of quinoidal oligothiophenes, from the dimer to the hexamer, with fused bis(butoxymethyl)cyclopentane groups has been extensively investigated by means of electronic and vibrational spectroscopy, electrochemical measurements, and density functional calculations. The latter predict that the electronic ground state always corresponds to a singlet state and that, for the longest oligomers, this state has biradical character that increases with increasing oligomer length. The shortest oligomers display closed-shell quinoidal structures. Calculations also predict the existence of very low energy excited triplet states that can be populated at room temperature. Aromatization of the conjugated carbon backbone is the driving force that determines the increasing biradical character of the ground state and the appearance of low-lying triplet states. UV/Vis, Raman, IR, and electrochemical experiments support the aromatic biradical structures predicted for the ground state of the longest oligomers and reveal that population of the low-lying triplet state accounts for the magnetic activity displayed by these compounds.

References

Apr 19, 2002·Journal of the American Chemical Society·Ted M PappenfusLarry L Miller
Oct 10, 2002·Journal of the American Chemical Society·Juan CasadoJuan T López Navarrete
May 14, 2004·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Juan CasadoJuan T López Navarrete
Jun 23, 2005·Journal of the American Chemical Society·Toshiaki TakahashiYoshio Aso
Jul 21, 2006·The Journal of Physical Chemistry. B·Anna BerlinJuan T López Navarrete
Jan 26, 2007·The Journal of Physical Chemistry. B·Alberto MilaniGiuseppe Zerbi

❮ Previous
Next ❯

Citations

Aug 22, 2015·Journal of the American Chemical Society·Longbin RenXiaozhang Zhu
Mar 19, 2015·Physical Chemistry Chemical Physics : PCCP·L ColellaC Bertarelli
Sep 14, 2018·Physical Chemistry Chemical Physics : PCCP·Sofia CanolaFabrizia Negri
Sep 7, 2018·Chemistry : a European Journal·Dennis RottschäferRajendra S Ghadwal
Nov 17, 2010·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Daniele FazziChiara Castiglioni
Mar 15, 2016·Journal of Molecular Modeling·Diego López-Carballeira, Fernando Ruipérez
Mar 20, 2020·Angewandte Chemie·Sebastian N IntorpUwe H F Bunz
Jan 13, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Anup Thomas, Kotamarthi Bhanuprakash
Mar 23, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Mamoru FujitsukaTetsuro Majima
Jul 24, 2015·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Juan CasadoJuan T López Navarrete
Apr 1, 2015·Chemical Science·Wangdong ZengJishan Wu
May 19, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Kyohei YonedaBenoît Champagne
Dec 3, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Juan AragóJuan T López Navarrete
Jul 19, 2012·Chemical Society Reviews·Juan CasadoJuan T López Navarrete
Feb 11, 2011·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Juan Casado, Juan T López Navarrete
Aug 9, 2011·The Journal of Physical Chemistry. B·Sandra Rodríguez GonzálezJuan Casado
Aug 12, 2015·The Journal of Physical Chemistry Letters·Oleg VarnavskiTheodore Goodson
Jul 26, 2013·Chemical Reviews·Manabu Abe
Sep 22, 2011·Journal of the American Chemical Society·Sandra R GonzálezJuan Casado
Jul 9, 2011·The Journal of Physical Chemistry. a·Masayoshi NakanoBenoît Champagne
Oct 24, 2012·Journal of the American Chemical Society·Eleonora V CanesiChiara Castiglioni
Apr 13, 2018·Chemical Reviews·David Casanova

❮ Previous
Next ❯

Related Concepts

Trending Feeds

COVID-19

Coronaviruses encompass a large family of viruses that cause the common cold as well as more serious diseases, such as the ongoing outbreak of coronavirus disease 2019 (COVID-19; formally known as 2019-nCoV). Coronaviruses can spread from animals to humans; symptoms include fever, cough, shortness of breath, and breathing difficulties; in more severe cases, infection can lead to death. This feed covers recent research on COVID-19.

Blastomycosis

Blastomycosis fungal infections spread through inhaling Blastomyces dermatitidis spores. Discover the latest research on blastomycosis fungal infections here.

Nuclear Pore Complex in ALS/FTD

Alterations in nucleocytoplasmic transport, controlled by the nuclear pore complex, may be involved in the pathomechanism underlying multiple neurodegenerative diseases including Amyotrophic Lateral Sclerosis and Frontotemporal Dementia. Here is the latest research on the nuclear pore complex in ALS and FTD.

Applications of Molecular Barcoding

The concept of molecular barcoding is that each original DNA or RNA molecule is attached to a unique sequence barcode. Sequence reads having different barcodes represent different original molecules, while sequence reads having the same barcode are results of PCR duplication from one original molecule. Discover the latest research on molecular barcoding here.

Chronic Fatigue Syndrome

Chronic fatigue syndrome is a disease characterized by unexplained disabling fatigue; the pathology of which is incompletely understood. Discover the latest research on chronic fatigue syndrome here.

Evolution of Pluripotency

Pluripotency refers to the ability of a cell to develop into three primary germ cell layers of the embryo. This feed focuses on the mechanisms that underlie the evolution of pluripotency. Here is the latest research.

Position Effect Variegation

Position Effect Variagation occurs when a gene is inactivated due to its positioning near heterochromatic regions within a chromosome. Discover the latest research on Position Effect Variagation here.

STING Receptor Agonists

Stimulator of IFN genes (STING) are a group of transmembrane proteins that are involved in the induction of type I interferon that is important in the innate immune response. The stimulation of STING has been an active area of research in the treatment of cancer and infectious diseases. Here is the latest research on STING receptor agonists.

Microbicide

Microbicides are products that can be applied to vaginal or rectal mucosal surfaces with the goal of preventing, or at least significantly reducing, the transmission of sexually transmitted infections. Here is the latest research on microbicides.