The electronic origin of the dual fluorescence in donor-acceptor substituted benzene derivatives

Journal of the American Chemical Society
Semyon CoganYehuda Haas

Abstract

The origin of the dual fluorescence of DMABN (dimethylaminobenzonitrile) and other benzene derivatives is explained by a charge transfer model based on the properties of the benzene anion radical. It is shown that, in general, three low-lying electronically excited states are expected for these molecules, two of which are of charge transfer (CT) character, whereas the third is a locally excited (LE) state. Dual fluorescence may arise from any two of these states, as each has a different geometry at which it attains a minimum. The Jahn-Teller induced distortion of the benzene anion radical ground state helps to classify the CT states as having quinoid (Q) and antiquinoid (AQ) forms. The intramolecular charge transfer (ICT) state is formed by the transfer of an electron from a covalently linked donor group to an anti-bonding orbital of the pi-electron system of benzene. The change in charge distribution of the molecule in the CT states leads to the most significant geometry change undergone by the molecule which is the distortion of the benzene ring to a Q or AQ structure. As the dipole moment is larger in the perpendicular geometry than in the planar one, this geometry is preferred in polar solvents, supporting the twisted intra...Continue Reading

References

Apr 26, 2003·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Toshitada YoshiharaKlaas A Zachariasse
Jan 30, 2004·Journal of the American Chemical Society·Dmitrij Rappoport, Filipp Furche
Jun 10, 2004·Journal of the American Chemical Society·Andreas Köhn, Christof Hättig
Jul 9, 2004·Journal of the American Chemical Society·Toshitada YoshiharaKlaas A Zachariasse
May 12, 2005·Journal of the American Chemical Society·Isabel GómezMichael A Robb

❮ Previous
Next ❯

Citations

May 18, 2010·Journal of Fluorescence·Tesfay AtsbehaMesfin Redi-Abshiro
Oct 10, 2015·The Journal of Chemical Physics·Andrew R DixonAndrei Sanov
Dec 16, 2016·The Journal of Physical Chemistry. a·Basile F E CurchodTodd J Martínez
Aug 30, 2014·Chemistry : a European Journal·Mikhail S BaranovIlia V Yampolsky
Oct 7, 2016·Physical Chemistry Chemical Physics : PCCP·Hsuan-Hsiao YaoI-Chia Chen
Mar 12, 2015·Physical Chemistry Chemical Physics : PCCP·Cheng Zhong
Feb 26, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Linna ZhuChuluo Yang
Mar 5, 2010·Physical Chemistry Chemical Physics : PCCP·Peter D ZoonAlbert M Brouwer
Apr 29, 2010·Physical Chemistry Chemical Physics : PCCP·Akitaka ItoNoboru Kitamura
Jun 18, 2010·Physical Chemistry Chemical Physics : PCCP·Guang-Jiu Zhao, Ke-Li Han
Apr 12, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Wooseok Heo, Taiha Joo
Feb 18, 2012·Physical Chemistry Chemical Physics : PCCP·Shmuel ZilbergYehuda Haas
Feb 3, 2012·Physical Chemistry Chemical Physics : PCCP·Francis A S ChipemG Krishnamoorthy
Aug 12, 2014·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Anasuya MishraG Krishnamoorthy
Oct 30, 2014·Physical Chemistry Chemical Physics : PCCP·Javier Segarra-Martí, Pedro B Coto
Dec 15, 2018·Journal of Computational Chemistry·Federica MaschiettoIlaria Ciofini
Sep 13, 2012·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Ali H Younes, Lei Zhu
Dec 7, 2018·Macromolecular Rapid Communications·Wei HuangUwe H F Bunz
Sep 26, 2013·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Wei Shyang TanJye-Shane Yang
Sep 12, 2020·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Liesbeth De BrueckerVeronique Van Speybroeck
Dec 5, 2020·Bioorganic & Medicinal Chemistry·Manuela PetacciaGiovanna Mancini
Jun 17, 2008·The Journal of Physical Chemistry. B·Silvia CarlottoVincenzo Barone
Sep 2, 2009·The Journal of Physical Chemistry. a·Sergey I DruzhininKlaas A Zachariasse
Apr 14, 2021·Nano Letters·Zhongwei ManHongbing Fu
Apr 23, 2021·Physical Chemistry Chemical Physics : PCCP·Rahul Gera, Jyotishman Dasgupta
Dec 20, 2012·The Journal of Physical Chemistry. a·Myeongkee ParkTaiha Joo
May 18, 2011·Journal of the American Chemical Society·Guorong SunKaren L Wooley
Aug 24, 2012·The Journal of Physical Chemistry. B·Adam J FleisherDavid W Pratt
Aug 14, 2012·Journal of Chemical Theory and Computation·Elena N LarichevaMassimo Olivucci

❮ Previous
Next ❯

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.