Anthraquinone derivatives as electron-acceptors with liquid crystalline properties

Physical Chemistry Chemical Physics : PCCP
Amy E MurschellTodd C Sutherland

Abstract

Dialkoxy derivatives of anthraquinone (AQ), dicyano-anthraquinone (DCAQ) and tetracyanoanthraquinone (TCAQ) were synthesized and their associated electrochemical, optical and self-assembling properties were investigated as candidates for n-type materials. AQ shows UV absorption features, whereas both DCAQ and TCAQ exhibit bathochromic and hyperchromic electronic transitions into the visible region. The electron accepting strength of the three compounds was established by cyclic voltammetry as -1.52 V, -1.3 V and -0.9 V vs. ferrocene/ferricenium for AQ, DCAQ and TCAQ, respectively. All three quinones displayed quasireversible, two sequential one-electron transfer redox reactions. DFT calculations of DCAQ and TCAQ demonstrate structural changes upon reduction, which is supported by spectroelectrochemical experiments. Furthermore, the structural changes result in different absorption profiles and show potential as electrochromic materials. Finally, both AQ and DCAQ show liquid crystalline phases and importantly, DCAQ exhibits both a smectic liquid crystalline and a soft crystal phase between -6 °C and 85 °C, which offers promise as a self-assembling n-type material.

References

May 2, 2000·The Journal of Organic Chemistry·K Takahashi, K Kobayashi
Aug 9, 2001·Journal of the American Chemical Society·B A Gregg, R A Cormier
Nov 15, 1996·The Journal of Organic Chemistry·Takahito ItohMasataka Kubo
Feb 12, 2004·Journal of the American Chemical Society·Robert L Donkers, Mark S Workentin
Mar 5, 2004·Physical Review. E, Statistical, Nonlinear, and Soft Matter Physics·S RauchA Jákli
Aug 12, 2004·Journal of the American Chemical Society·Jeroen van HerrikhuyzenE W Meijer
Jun 1, 2006·Journal of the American Chemical Society·Kaushik BalakrishnanLing Zang
Jun 29, 2006·Journal of the American Chemical Society·E Johan FosterVance E Williams
Dec 5, 2006·Chemistry : a European Journal·Zhijian ChenFrank Würthner
Dec 15, 2006·Chemical Reviews·John E Anthony
Apr 13, 2007·Chemical Reviews·Amanda R Murphy, Jean M J Fréchet
Nov 6, 2007·Chemical Society Reviews·Sergey SergeyevYves Henri Geerts
Sep 16, 2008·Journal of the American Chemical Society·Hon Hang FongMichael Sorensen
Sep 26, 2008·Chemical Communications : Chem Comm·Emilio M PérezNazario Martín
Apr 11, 2009·Chemical Communications : Chem Comm·Masashi MamadaYoshiro Yamashita
Sep 22, 2009·Journal of the American Chemical Society·André WickleinMukundan Thelakkat
Jul 2, 2010·Langmuir : the ACS Journal of Surfaces and Colloids·Amy E Murschell, Todd C Sutherland
Dec 3, 2010·Chemical Communications : Chem Comm·Sabin-Lucian SuraruFrank Würthner
Feb 5, 2011·Chemistry : a European Journal·José SantosDirk M Guldi
Mar 31, 2011·Advanced Materials·Zhixiong LiangQian Miao
Jun 21, 2011·ACS Applied Materials & Interfaces·Teresa L ChenBiwu Ma

❮ Previous
Next ❯

Citations

May 6, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Hande UnsalNihal Aydogan
Jul 28, 2015·Physical Chemistry Chemical Physics : PCCP·K D ThériaultT C Sutherland
Jun 18, 2015·Physical Chemistry Chemical Physics : PCCP·S CospitoG Chidichimo
Oct 17, 2017·Chemistry : a European Journal·Marco GruberRik R Tykwinski

❮ 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.

Related Papers

Langmuir : the ACS Journal of Surfaces and Colloids
Amy E Murschell, Todd C Sutherland
Langmuir : the ACS Journal of Surfaces and Colloids
Jean-Paul DouliezFrédéric Nallet
© 2022 Meta ULC. All rights reserved