Spacer-Modulated Differentiation Between Self-Assembly and Folding Pathways for Bichromophoric Merocyanine Dyes

Chemistry : a European Journal
André Zitzler-KunkelFrank Würthner

Abstract

We have synthesized a large series of bis(merocyanine) dyes with varying spacer unit and investigated in detail their self-organization behavior by concentration- as well as solvent-dependent UV/Vis spectroscopy. Our in-depth studies have shown that the self-organization of the present bis(merocyanine) dyes is subtly influenced by the nature of the spacer unit. The utilization of rigid spacers results in the formation of self-associated bimolecular complexes with high binding strength, while flexible spacers drive the respective bichromophoric dyes to intramolecular folding. Our thorough investigations on the impact of alkyl spacer chain length on the folding tendency of the present series of bis(merocyanine) dyes revealed a biphasic behavior, that is, a steep increase of the folding tendency for the dyes containing C4 to C7 chains and then a gentle decrease for dyes with longer alkyl spacer chains as evidenced by free energy (ΔG) values for the folding of these dyes. Furthermore, analyses of aggregates' optical properties based on exciton theory as well as quantum chemical calculations suggest a bimolecular aggregate structure for the dye possessing a rigid spacer and a rotationally twisted pleated structure for the bis(merocy...Continue Reading

References

Aug 9, 2001·Journal of the American Chemical Society·S Zeena, K G Thomas
Dec 12, 2001·Current Opinion in Chemical Biology·M S Cubberley, B L Iverson
Dec 19, 1996·Chemical Reviews·R. Bruce Martin
Dec 12, 2002·Journal of the American Chemical Society·Joel P SchneiderJuliana Kretsinger
Oct 21, 2003·Chemistry : a European Journal·Alexander D Q LiLi-Qiong Wang
Dec 17, 2003·Accounts of Chemical Research·Frank-Gerrit Klärner, Björn Kahlert
Mar 3, 2005·Journal of the American Chemical Society·Easwaran ArunkumarJörg Daub
Oct 3, 2006·Angewandte Chemie·Ulrich RöschFrank Würthner
Mar 24, 2007·Chemical Reviews·Veaceslav CoropceanuJean-Luc Brédas
Jul 2, 2008·Accounts of Chemical Research·W Seth Horne, Samuel H Gellman
Aug 30, 2008·Accounts of Chemical Research·Liam C Palmer, Samuel I Stupp
Jan 27, 2009·Chemical Society Reviews·Zhijian ChenFrank Würthner
Jul 10, 2009·Chemical Society Reviews·Ishu Saraogi, Andrew D Hamilton
Sep 12, 2009·Angewandte Chemie·Christopher A Hunter, Harry L Anderson
Sep 23, 2009·Chemical Reviews·Tom F A De GreefE W Meijer
Dec 18, 2009·Accounts of Chemical Research·Frank C Spano
Mar 29, 2011·Angewandte Chemie·Frank WürthnerChantu R Saha-Möller
Apr 13, 2011·Chemical Communications : Chem Comm·Gilles Guichard, Ivan Huc
Feb 22, 2012·Science·T AidaS I Stupp
Aug 9, 2012·Chemical Reviews·Dan-Wei ZhangZhan-Ting Li
Mar 13, 2013·Accounts of Chemical Research·John D Tovar
Jan 10, 2014·Chemical Reviews·Sukumaran Santhosh BabuAyyappanpillai Ajayaghosh
Jun 27, 2014·Journal of the American Chemical Society·Edward J DaleJ Fraser Stoddart
Aug 21, 2014·Chemical Communications : Chem Comm·Anindita Das, Suhrit Ghosh
Dec 17, 2014·Journal of the American Chemical Society·Won Min Park, Julie A Champion

❮ Previous
Next ❯

Citations

Feb 4, 2016·Chemical Communications : Chem Comm·David BialasFrank Würthner
May 14, 2017·Chemistry : a European Journal·Łukasz KielesińskiDaniel T Gryko
May 17, 2018·Physical Chemistry Chemical Physics : PCCP·Łukasz KielesińskiOlaf W Morawski
Sep 22, 2018·Physical Chemistry Chemical Physics : PCCP·Olatz Uranga-BarandiaranDavid Casanova
Jan 17, 2020·Chemistry : a European Journal·Manon CatherinFrédéric Fages
Mar 16, 2021·Journal of the American Chemical Society·David BialasFrank Würthner
Feb 1, 2020·Journal of the American Chemical Society·Xiaobo HuFrank Würthner
Nov 12, 2020·Journal of the American Chemical Society·Mathijs F J MabesooneE W Meijer

❮ 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.