Synthetic Methods Driven by the Photoactivity of Electron Donor-Acceptor Complexes

Journal of the American Chemical Society
Giacomo E M CrisenzaPaolo Melchiorre

Abstract

The association of an electron-rich substrate with an electron-accepting molecule can generate a new molecular aggregate in the ground state, called an electron donor-acceptor (EDA) complex. Even when the two precursors do not absorb visible light, the resulting EDA complex often does. In 1952, Mulliken proposed a quantum-mechanical theory to rationalize the formation of such colored EDA complexes. However, and besides a few pioneering studies in the 20th century, it is only in the past few years that the EDA complex photochemistry has been recognized as a powerful strategy for expanding the potential of visible-light-driven radical synthetic chemistry. Here, we explain why this photochemical synthetic approach was overlooked for so long. We critically discuss the historical context, scientific reasons, serendipitous observations, and landmark discoveries that were essential for progress in the field. We also outline future directions and identify the key advances that are needed to fully exploit the potential of the EDA complex photochemistry.

References

Feb 24, 2006·Angewandte Chemie·Mark S Taylor, Eric N Jacobsen
Sep 27, 1912·Science·G Ciamician
Apr 3, 2008·Accounts of Chemical Research·Sergiy V Rosokha, Jay K Kochi
Jul 31, 2008·Angewandte Chemie·Paolo MelchiorreGiuseppe Bartoli
Sep 5, 2008·Journal of the American Chemical Society·Michael A IschayTehshik P Yoon
Sep 19, 2008·Nature·David W C MacMillan
May 8, 2009·Chemical Society Reviews·Zhiguo Zhang, Peter R Schreiner
Jun 26, 2009·Journal of the American Chemical Society·Jagan M R NarayanamCorey R J Stephenson
Dec 9, 2009·Journal of the American Chemical Society·Guillaume BerionniRégis Goumont
Jan 15, 2010·Current Opinion in Chemical Biology·Gjalt W HuismanAnke Krebber
Mar 2, 2013·Angewandte Chemie·Seiji Shirakawa, Keiji Maruoka
May 2, 2013·Dalton Transactions : an International Journal of Inorganic Chemistry·Santiago Alvarez
Mar 1, 2014·Science·Danielle M Schultz, Tehshik P Yoon
Mar 29, 2014·Angewandte Chemie·Manuel NappiPaolo Melchiorre
Mar 29, 2014·Angewandte Chemie·Daniel A DiroccoMatthew Tudge
Dec 17, 2014·Nature·Kyle W Quasdorf, Larry E Overman
Apr 23, 2015·Journal of the American Chemical Society·Łukasz WoźniakPaolo Melchiorre
Apr 25, 2015·Chemistry : a European Journal·Yuanzheng ChengShouyun Yu
May 21, 2015·Chemical Reviews·Darrin M FlaniganTomislav Rovis
May 28, 2015·Chemistry : a European Journal·Juan Antonio Maciá-AgullóHermenegildo Garcia
Oct 16, 2015·Angewandte Chemie·Armido Studer, Dennis P Curran
Oct 27, 2015·Journal of the American Chemical Society·Christopher K Prier, Frances H Arnold
Mar 15, 2016·Angewandte Chemie·Todd K Hyster, Thomas R Ward
Apr 19, 2016·Angewandte Chemie·Mark L SpellJustin R Ragains
May 18, 2016·Journal of the American Chemical Society·Valentin QuintSami Lakhdar
Jun 9, 2016·Journal of the American Chemical Society·Ana Bahamonde, Paolo Melchiorre
Jun 11, 2016·Chemical Reviews·Nathan A Romero, David A Nicewicz
Aug 2, 2016·The Journal of Organic Chemistry·Megan H ShawDavid W C MacMillan
Sep 16, 2016·Journal of the American Chemical Society·Ming YanPhil S Baran
Mar 11, 2017·Journal of the American Chemical Society·Ana BahamondePaolo Melchiorre
Jun 18, 2017·Science·Alexander FawcettVarinder K Aggarwal
Sep 15, 2017·Journal of the American Chemical Society·Bin LiuGarret M Miyake
Oct 25, 2017·Angewandte Chemie·Frances H Arnold
Nov 18, 2017·Chemical Science·Xinjun Tang, Armido Studer
Nov 23, 2017·Angewandte Chemie·Xinjun Tang, Armido Studer
Feb 2, 2018·Nature·Mattia Silvi, Paolo Melchiorre
Feb 20, 2018·Angewandte Chemie·Leyre MarzoBurkhard König
Aug 1, 2018·Chemistry : a European Journal·Cecilia Bottecchia, Timothy Noël
Aug 10, 2018·Journal of the American Chemical Society·Jingjing WuVarinder K Aggarwal

❮ Previous
Next ❯

Citations

May 28, 2020·Organic & Biomolecular Chemistry·Bor-Cherng Hong
Aug 26, 2020·Angewandte Chemie·Chris SlootwegBas de Bruin
Jun 20, 2020·Beilstein Journal of Organic Chemistry·Stephanie G E AmosJerome Waser
Sep 25, 2020·Chemical Communications : Chem Comm·Thomas Rigotti, José Alemán
Apr 8, 2020·Chemistry : a European Journal·Flip HoltropJ Chris Slootweg
Sep 17, 2020·Chemistry, an Asian Journal·Savita B NagodeNamrata Rastogi
Oct 21, 2020·Organic & Biomolecular Chemistry·Kathleen J Berger, Mark D Levin
Oct 22, 2020·Beilstein Journal of Organic Chemistry·Callum PrenticeEli Zysman-Colman
Dec 15, 2020·Chemical Society Reviews·Nikita Kvasovs, Vladimir Gevorgyan
Oct 2, 2020·Angewandte Chemie·Matthias SchmalzbauerBurkhard König
Dec 2, 2020·Chemistry : a European Journal·Yuya NakatsujiYoshiji Takemoto
Jan 1, 2021·Journal of the American Chemical Society·Braddock A SandovalTodd K Hyster
Feb 18, 2021·Organic Letters·Chao-Shen ZhangXiang-Yu Chen
Sep 22, 2020·The Journal of Organic Chemistry·Di QiuStefano Protti
Feb 25, 2021·Chemical Communications : Chem Comm·Ana M Martínez-GualdaJosé Alemán
Mar 16, 2021·The Journal of Organic Chemistry·Min HeMing Bao
Apr 7, 2021·The Journal of Organic Chemistry·Dhananjay YadavMaya Shankar Singh
Apr 24, 2021·Chemical Society Reviews·Yuto Sumida, Hirohisa Ohmiya
Apr 24, 2021·Beilstein Journal of Organic Chemistry·Zhonglie YangJiahong Li
May 25, 2021·Journal of the American Chemical Society·Yang JiaoJ Fraser Stoddart
May 29, 2021·Chemical Society Reviews·Mohammed Latrache, Norbert Hoffmann
Jun 1, 2021·ACS Central Science·Changmin XieOhyun Kwon
Jun 8, 2021·Chemical Science·Timothée ConstantinDaniele Leonori
Jun 12, 2021·Journal of the American Chemical Society·Haigen FuTodd K Hyster
Jun 15, 2021·The Journal of Organic Chemistry·Robert M Ward, Jennifer M Schomaker
May 11, 2021·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·William LecroqSami Lakhdar
Jun 15, 2021·Chemical Science·Mirjam R SchreierOliver S Wenger

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray

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.