Theoretical and experimental investigations of circular dichroism and absolute configuration determination of chiral anthracene photodimers

Journal of the American Chemical Society
Ayako WakaiYoshihisa Inoue

Abstract

Substituted anthracenes photodimerize to stereoisomeric [4 + 4] cyclodimers, some of which are inherently chiral. Recent supramolecular photochirogenic studies enabled the efficient preparation of specific stereoisomers, the absolute configurations of which should reflect the chiral environment of supramolecular host or scaffold employed but have not been determined, hindering detailed mechanistic elucidation and further host/scaffold design. In this study, we performed the combined experimental and state-of-the-art theoretical analyses of the circular dichroism spectra of chiral cyclodimers of 2-anthracenecarboxylic and 2,6-anthracenedicarboxylic acids to reveal the configurational and molecular orbital origin of the Cotton effects observed, and unambiguously determined the absolute configurations of these chiral cyclodimers. The present results allow us to directly correlate the enantiotopic face-selectivity upon photocyclodimerization with the absolute configuration of the cyclodimer derived therefrom and also to precisely elucidate the chiral arrangement of two cyclodimerizing anthracenes.

References

Jul 22, 2004·Journal of the American Chemical Society·Toshihiro IharaAkinori Jyo
Mar 18, 2005·Journal of the American Chemical Society·Lakshmi S KaanumalleV Ramamurthy
Nov 10, 2005·Chemical Reviews·Andreas Dreuw, Martin Head-Gordon
Jun 16, 2006·The Journal of Physical Chemistry. a·Timothy D KowalczykT Daniel Crawford
Mar 6, 2007·Journal of the American Chemical Society·Masaki NishijimaYoshihisa Inoue
May 10, 2007·The Journal of Physical Chemistry. a·Mary C TamT Daniel Crawford
Jul 17, 2007·The Journal of Physical Chemistry. a·Tadashi MoriStefan Grimme
Dec 22, 2007·Chemical Reviews·Guy A HemburyYoshihisa Inoue
May 24, 2008·The Journal of Organic Chemistry·Masahiko ShibaharaTeruo Shinmyozu
Oct 22, 2008·The Journal of Organic Chemistry·Atsuya MuranakaNagao Kobayashi
Dec 24, 2008·The Journal of Physical Chemistry. a·Lars Goerigk, Stefan Grimme
Apr 11, 2009·Chemical Communications : Chem Comm·Arnab DawnSeiji Shinkai
Jan 2, 2010·Journal of the American Chemical Society·Gerhard BringmannFrank Meyer
May 6, 2010·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Kazuki BandoYoshihisa Inoue
Jun 10, 2011·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Jan-Michael MewesAndreas Dreuw
Jun 30, 2011·Journal of the American Chemical Society·Sanjio S ZadeMichael Bendikov
Jan 10, 2012·Journal of Chemical Theory and Computation·Monika Srebro, Jochen Autschbach

❮ Previous
Next ❯

Citations

Nov 20, 2015·Spectrochimica Acta. Part A, Molecular and Biomolecular Spectroscopy·Balázs KomjátiPéter Horváth
Oct 25, 2016·Journal of the American Chemical Society·Akifumi TakanabeToru Asahi
Feb 12, 2017·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Hiroki TanakaTadashi Mori
Dec 3, 2013·Chemical Society Reviews·Cheng Yang, Yoshihisa Inoue
Sep 24, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Cheng YangYoshihisa Inoue
Aug 2, 2013·Chemical Communications : Chem Comm·Masaki NishijimaYoshihisa Inoue
Nov 7, 2013·Acta Crystallographica. Section C, Crystal Structure Communications·Yuko KawanamiYoshihisa Inoue
Nov 21, 2017·Journal of Computational Chemistry·Sandro JurinovichBenedetta Mennucci
Jun 4, 2021·Journal of the American Chemical Society·Xiao-Yang ChenJ Fraser Stoddart
Aug 12, 2014·Journal of Chemical Theory and Computation·Zlatko BrkljačaAna-Sunčana Smith
May 22, 2013·The Journal of Physical Chemistry. a·Yoshito NakaiYoshihisa Inoue
Dec 5, 2012·The Journal of Physical Chemistry. a·Yoshito NakaiYoshihisa Inoue
Aug 25, 2012·The Journal of Physical Chemistry. a·Mitsunobu TodaTadashi Mori
Oct 15, 2021·Chemical Communications : Chem Comm·Wei-Lei ZhouYu Liu

❮ 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.