Discrete and polymeric self-assembled dendrimers: hydrogen bond-mediated assembly with high stability and high fidelity

Proceedings of the National Academy of Sciences of the United States of America
Perry S CorbinSteven C Zimmerman

Abstract

Hydrogen bond-mediated self-assembly is a powerful strategy for creating nanoscale structures. However, little is known about the fidelity of assembly processes that must occur when similar and potentially competing hydrogen-bonding motifs are present. Furthermore, there is a continuing need for new modules and strategies that can amplify the relatively weak strength of a hydrogen bond to give more stable assemblies. Herein we report quantitative complexation studies on a ureidodeazapterin-based module revealing an unprecedented stability for dimers of its self-complementary acceptor-acceptor-donor-donor (AADD) array. Linking two such units together with a semirigid spacer that carries a first-, second-, or third-generation Fréchet-type dendron affords a ditopic structure programmed to self assemble. The specific structure that is formed depends both on the size of the dendron and the solvent, but all of the assemblies have exceptionally high stability. The largest discrete nanoscale assembly is a hexamer with a molecular mass of about 17.8 kDa. It is stabilized by 30 hydrogen bonds, including six AADD x DDAA contacts. The hexamer forms and is indefinitely stable in the presence of a hexamer containing six ADD x DAA hydrogen-bo...Continue Reading

References

Feb 1, 1966·Die Naturwissenschaften·M Eigen, L de Maeyer
Feb 23, 1996·Science·S C ZimmermanS V Kolotuchin
Jul 8, 1997·Proceedings of the National Academy of Sciences of the United States of America·R K CastellanoJ Rebek
Dec 26, 2001·Chemical Reviews·S LeiningerP J Stang
Feb 19, 2002·Chemical Reviews·Françisco M. Raymo, J. Fraser Stoddart
Aug 5, 1997·Chemical Reviews·M. Morgan Conn, Julius Rebek

❮ Previous
Next ❯

Citations

Aug 19, 2011·Chemical Reviews·Marina M Safont-SempereFrank Würthner
Apr 19, 2011·Journal of the American Chemical Society·Dongwon Shin, Yitzhak Tor
Jul 20, 2012·Journal of the American Chemical Society·Peter A KorevaarE W Meijer
Aug 27, 2009·Journal of the American Chemical Society·Naoki TomimasuAkira Harada
Nov 13, 2009·Journal of the American Chemical Society·Stephan A SchmidLaura M Herz
Mar 21, 2012·The Journal of Organic Chemistry·Qing HanHai-Bo Yang
Aug 29, 2012·The Journal of Organic Chemistry·Wei-Jun ChuZhigang Shuai
Apr 7, 2006·Organic Letters·Hugo C Ong, Steven C Zimmerman
Mar 20, 2013·Organic Letters·Laura J Marshall, Javier de Mendoza
Feb 24, 2005·Chemical Society Reviews·Henk M Keizer, Rint P Sijbesma
Oct 6, 2010·Proceedings of the National Academy of Sciences of the United States of America·Pol BeseniusE W Meijer
Aug 10, 2016·The Journal of Physical Chemistry. B·Anita S W Chan, Pudupadi R Sundararajan
Jul 28, 2016·Langmuir : the ACS Journal of Surfaces and Colloids·Sylvain CatrouilletOlivier Colombani
Nov 3, 2016·Journal of the American Chemical Society·Avik SamantaJ Fraser Stoddart
Jan 16, 2013·Scientific Reports·Yong YangJunfeng Xiang
Jan 3, 2014·Chemistry : a European Journal·Koushik Acharyya, Partha Sarathi Mukherjee
Jun 17, 2016·ChemistryOpen·María J MayoralDavid González-Rodríguez
Oct 16, 2004·Angewandte Chemie·Kwangyul MoonAngel E Kaifer
Oct 3, 2007·Dalton Transactions : an International Journal of Inorganic Chemistry·Michael J CowleyAdrian C Whitwood
Jun 17, 2005·Chemistry : a European Journal·Henk M KeizerJavier de Mendoza
Jun 18, 2009·Chemistry : a European Journal·Bilge BaytekinChristoph A Schalley
Aug 3, 2013·Physical Chemistry Chemical Physics : PCCP·Gunjan Verma, P A Hassan
Apr 18, 2012·Beilstein Journal of Organic Chemistry·Yagang Zhang, Steven C Zimmerman
Jan 24, 2012·Chemistry : a European Journal·Partha S Ghosh, Andrew D Hamilton
Sep 22, 2012·Chemistry : a European Journal·Bhanu P Mudraboyina, James A Wisner
Jan 4, 2013·Chemical Communications : Chem Comm·Chun-Ho Wong, Steven C Zimmerman
Jun 23, 2009·Chemistry : a European Journal·Yao-Rong ZhengPeter J Stang
Nov 30, 2013·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Alfredo Henrique Duarte LopezÉder Henrique da Silva
Dec 15, 2015·Beilstein Journal of Organic Chemistry·Karina MroczyńskaBorys Ośmiałowski

❮ 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.