The (photo)chemistry of Stenhouse photoswitches: guiding principles and system design

Chemical Society Reviews
Michael M LerchBen L Feringa

Abstract

Molecular photoswitches comprise chromophores that can be interconverted reversibly with light between two states with different photochemical and physicochemical properties. This feature renders them useful for diverse applications, ranging from materials science, biology (specifically photopharmacology) to supramolecular chemistry. With new and more challenging systems to control, especially extending towards biomedical applications, using visible or near-infrared light for photoswitch activation becomes vital. Donor-acceptor Stenhouse adducts are a novel class of visible light-responsive negative photochromes that provide a possible answer to current limitations of other photoswitch classes in the visible and NIR window. Their rapid development since their discovery in 2014, together with first successful examples of applications, demonstrate both their potential and areas where improvements are needed. A better understanding of DASA characteristics and its photoswitching mechanism has revealed that they are in fact a subset of a more general structural class of photochromes, namely Stenhouse photoswitches. This tutorial review aims at providing an introduction and practical guide on DASAs: it focuses on their structure and ...Continue Reading

References

Jan 12, 2001·Journal of Photochemistry and Photobiology. B, Biology·S StolikL Anasagasti
Jan 7, 2003·Nature Medicine·Ralph Weissleder, Vasilis Ntziachristos
May 13, 2004·Chemical Reviews·Vladimir I Minkin
Sep 8, 2004·Chemistry : a European Journal·Olalla Nieto FazaAngel R de Lera
Jul 26, 2012·Angewandte Chemie·Clara BriekeAlexander Heckel
Oct 11, 2013·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Claudia Piutti, Francesca Quartieri
Jan 25, 2014·Journal of the American Chemical Society·Willem A VelemaBen L Feringa
May 23, 2014·Journal of the American Chemical Society·Sameh HelmyJavier Read de Alaniz
Nov 13, 2014·The Journal of Organic Chemistry·Sameh HelmyJavier Read de Alaniz
Apr 30, 2015·Chemical Society Reviews·Arnaud FiheyDenis Jacquemin
Jun 23, 2015·Angewandte Chemie·David Bléger, Stefan Hecht
Jun 24, 2015·Accounts of Chemical Research·Johannes BroichhagenDirk Trauner
Sep 29, 2015·Accounts of Chemical Research·Mingxin DongG Andrew Woolley
Feb 13, 2016·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Adèle D LaurentDenis Jacquemin
May 7, 2016·Journal of the American Chemical Society·Michael M LerchBen L Feringa
Jul 5, 2016·Angewandte Chemie·Michael M LerchBen L Feringa
Jul 13, 2016·Nature Communications·Michael M LerchBen L Feringa
Aug 6, 2016·Chemical Communications : Chem Comm·Saemi O PoelmaJavier Read de Alaniz
Oct 5, 2016·Journal of the American Chemical Society·James R HemmerJavier Read de Alaniz
Nov 3, 2016·Chemical Communications : Chem Comm·Neil MalloJonathon E Beves
Jan 27, 2017·Chemistry : a European Journal·Yvonne J DiazJavier Read de Alaniz
Oct 19, 2017·Journal of the American Chemical Society·Mariangela Di DonatoBen L Feringa
Nov 1, 2017·Organic & Biomolecular Chemistry·Martín J RiveiraMirta P Mischne
Dec 26, 2017·The Journal of Physical Chemistry. a·Michael M LerchBen L Feringa

❮ Previous
Next ❯

Citations

May 31, 2018·Angewandte Chemie·Michael M LerchBen L Feringa
Aug 7, 2018·Chemical Communications : Chem Comm·Tian-Guang ZhanKang-Da Zhang
Sep 29, 2018·Organic & Biomolecular Chemistry·Karin RustlerBurkhard König
Sep 20, 2018·Chemistry : a European Journal·Ronghua LiuLidong Li
Oct 31, 2018·Physical Chemistry Chemical Physics : PCCP·Claire TonneléFrédéric Castet
Jan 8, 2019·Chemistry : a European Journal·Zbigniew L Pianowski
May 2, 2019·Chemical Communications : Chem Comm·Mihael A GerkmanGrace G D Han
May 16, 2019·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Brandon F LuiChristopher J Bardeen
Aug 9, 2019·Chemistry : a European Journal·Amandine BoulmierOlivier Oms
Jan 15, 2020·Dalton Transactions : an International Journal of Inorganic Chemistry·Rupak Saha, Partha Sarathi Mukherjee
Nov 19, 2019·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Eduardo CarrascosaEvan J Bieske
Jan 9, 2020·Journal of Physics. Condensed Matter : an Institute of Physics Journal·Xin YuXin Bao
Jun 5, 2019·Nature Communications·Mark W H HoorensWiktor Szymanski
Aug 11, 2020·Macromolecular Rapid Communications·Jeaniffer E YapMartina H Stenzel
Jul 14, 2020·Macromolecular Rapid Communications·Nathan R B Boase
Mar 16, 2019·Frontiers in Chemistry·Juan PangXiaohong Hu
May 27, 2020·Nature Communications·Serena SeshadriMegan T Valentine
May 21, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Guillaume NoirbentFrédéric Dumur
Jul 18, 2018·Proceedings of the National Academy of Sciences of the United States of America·Jared D HarrisIvan Aprahamian
Dec 22, 2020·Chemical Communications : Chem Comm·Robin KlimekAlexander Heckel
Jan 26, 2021·Physical Chemistry Chemical Physics : PCCP·Sean W ConnollyHelena J Shepherd
Dec 2, 2020·Chemistry : a European Journal·David Martínez-LópezDiego Sampedro
Dec 22, 2020·Chemistry : a European Journal·Miranda M SrodaJavier Read de Alaniz
Oct 30, 2020·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Liam PayneBrian D Wagner
Sep 17, 2020·Angewandte Chemie·Shaoyu ChenBen L Feringa
Mar 2, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Dalma Edit NánásiGábor London
Mar 18, 2021·Langmuir : the ACS Journal of Surfaces and Colloids·Tetsuo YamaguchiMakoto Ogawa
Mar 23, 2021·Inorganic Chemistry·Nicholas D ShepherdDeanna M D'Alessandro
Sep 4, 2020·Journal of the American Chemical Society·Wenxin FuJennifer Q Lu
Mar 27, 2021·Chemistry : a European Journal·Anna-Lena LeistnerZbigniew L Pianowski
May 6, 2021·Organic & Biomolecular Chemistry·Andrey G Lvov, Aleksei Bredihhin
May 25, 2021·Small·Sebastian UlrichLuciano Fernandes Boesel
Jun 8, 2021·Chemical Science·Ilse M WellemanWiktor Szymański
Jul 9, 2021·Analytical Chemistry·Chao ZhengChongzhao Ran
Jun 2, 2018·Journal of the American Chemical Society·Omar Rifaie-GrahamNico Bruns

❮ Previous
Next ❯

Methods Mentioned

BETA
column chromatography
NMR
PMA
dynamic light scattering

Software Mentioned

DASAs

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.