Hierarchical formation of helical supramolecular polymers via stacking of hydrogen-bonded pairs in water

Proceedings of the National Academy of Sciences of the United States of America
L BrunsveldE W Meijer

Abstract

Bifunctional ureido-s-triazines provided with penta(ethylene oxide) side chains are able to self assemble in water, leading to helical columns via cooperative stacking of the hydrogen-bonded pairs (DADA array). Monofunctional ureido-s-triazines do not form such helical architectures. The presence of a linker, covalently connecting the two ureido-s-triazine units, is essential as it generates a high local concentration of aromatic units, favorable for stacking interactions. This hydrophobic stacking of the aromatic units occurs at concentrations as low as 5 x 10(-6) M and can be visualized by using fluorescence spectroscopy. The stacking generates a hydrophobic microenvironment that allows intermolecular hydrogen bonding to occur at higher concentrations because the hydrogen bonds are shielded from competitive hydrogen bonding with water. This hierarchical process results in the formation of a helical self-assembled polymer in water at concentrations above 10(-4) M. Chiral side chains attached to the ureido-s-triazine units bias the helicity of these columns as concluded from CD spectroscopy and "Sergeants and Soldiers" experiments.

References

Feb 14, 1995·Proceedings of the National Academy of Sciences of the United States of America·Y KatoJ Rebek
Jan 29, 2000·Angewandte Chemie·R B PrinceJ S Moore
Jul 8, 1997·Proceedings of the National Academy of Sciences of the United States of America·R K CastellanoJ Rebek
Jul 18, 2001·Journal of the American Chemical Society·H FenniriJ G Stowell
Jan 1, 1993·Proceedings of the National Academy of Sciences of the United States of America·T Gulik-KrzywickiJ Lehn
Apr 1, 1994·Journal of the American Chemical Society·J S NowickG Noronha

❮ Previous
Next ❯

Citations

Jul 2, 2005·Chirality·Jing ZhangJames W Canary
Dec 4, 2003·Current Opinion in Chemical Biology·Nobuo Kimizuka
May 1, 2010·Journal of the American Chemical Society·Tomohisa Sawada, Makoto Fujita
Apr 6, 2012·Journal of the American Chemical Society·Giovanni SalassaArjan W Kleij
Nov 3, 2009·Journal of the American Chemical Society·Mingming MaDennis Bong
Jun 22, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Mingming Ma, Dennis Bong
Feb 24, 2005·Chemical Society Reviews·Henk M Keizer, Rint P Sijbesma
Dec 1, 2007·Chemical Communications : Chem Comm·Ho Yong LeeJong-In Hong
Dec 20, 2015·Journal of the American Chemical Society·Hae-Geun JeonKyu-Sung Jeong
Apr 1, 2015·Proceedings of the National Academy of Sciences of the United States of America·Joonwoo JeongA G Yodh
Jan 5, 2016·Chemical Reviews·Elisha KriegBoris Rybtchinski
Aug 24, 2016·Journal of the American Chemical Society·Xiaoyu LiIan Manners
Feb 18, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Yi-Fei HanHong-Bo Wang
Mar 14, 2017·Journal of the American Chemical Society·Antoine GoujonNicolas Giuseppone
Feb 17, 2009·Angewandte Chemie·Leonard J Prins, Paolo Scrimin
Apr 22, 2016·Chemical Communications : Chem Comm·Anindita Das, Suhrit Ghosh
Aug 23, 2016·Chemical Communications : Chem Comm·Keith B SutyakJeffery T Davis
Jul 22, 2014·Angewandte Chemie·Kristof Van HeckeLuc Van Meervelt
Nov 14, 2014·Advanced Materials·Ruijiao DongJian Shen
Jul 20, 2007·Angewandte Chemie·Kunihiko ToyofukuTakuzo Aida
Oct 16, 2007·Angewandte Chemie·Anja R A Palmans, E W Meijer
Oct 19, 2007·Organic & Biomolecular Chemistry·Rika IwauraToshimi Shimizu
Mar 21, 2008·Dalton Transactions : an International Journal of Inorganic Chemistry·Anna CompanyMiquel Costas
May 28, 2008·Chemistry : a European Journal·Seong Ryong NamJong-In Hong
Jul 22, 2010·Chemistry : a European Journal·Dmitry S TuryginMaria A Kalinina
Mar 3, 2011·Chemistry : a European Journal·Tomohiro SekiShiki Yagai
Oct 13, 2007·Physical Review Letters·Szilard N Fejer, David J Wales
Nov 6, 2012·Chemical Communications : Chem Comm·Barnaby W GreenlandHoward M Colquhoun
Nov 9, 2012·Macromolecular Rapid Communications·Arthur BertrandJulien Bernard
Jul 30, 2005·Angewandte Chemie·Suhrit Ghosh, S Ramakrishnan
Feb 16, 2012·Organic & Biomolecular Chemistry·Hui ShaoJon R Parquette
Jun 30, 2015·Chemistry : a European Journal·Jiang-Fei XuXi Zhang
Jun 20, 2008·Soft Matter·Dirk Pijper, Ben L Feringa
Jun 3, 2011·Chemistry, an Asian Journal·Eun-Kyoung BangByeang Hyean Kim

❮ 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.

Related Papers

Proceedings of the National Academy of Sciences of the United States of America
Stephen E MillerParamjit S Arora
Combinatorial Chemistry & High Throughput Screening
Angel Díaz-OrtizAbel de Cózar
© 2022 Meta ULC. All rights reserved