Rational design of nanofibers and nanorings through complementary hydrogen-bonding interactions of functional pi systems

Chemistry : a European Journal
Shiki YagaiAyyappanpillai Ajayaghosh

Abstract

A simple protocol to create nanofibers and -rings through a rational self-assembly approach is described. Whereas the melamine-oligo(p-phenylenevinylene) conjugate 1a self-aggregates to form ill-defined nanostructures, conjugate 1b, which possesses an amide group as an additional interactive site, self-aggregates to form 1D nanofibers that induce gelation of the solvent. AFM and XRD studies have shown that dimerization through the melamine-melamine hydrogen-bonding interaction occurs only for 1b. Upon complexation with 1/3 equivalents of cyanuric acid (CA), conjugate 1a provides well-defined, ring-shaped nanostructures at micromolar concentrations, which open to form fibrous assemblies at submillimolar concentrations and organogels in the millimolar concentration range. Apparently, the enhanced aggregation ability of 1a by CA is a consequence of columnar organization of the resulting discotic complex 1a(3).CA. In contrast, coaggregation of 1b with CA does not provide well-defined nanostructures, probably due to the interference of complementary hydrogen-bonding interactions by the amide group.

References

Jul 10, 2001·Angewandte Chemie·Leonard J. PrinsPeter Timmerman
Aug 30, 2001·Proceedings of the National Academy of Sciences of the United States of America·L J PrinsD N Reinhoudt
Dec 26, 2001·Chemical Reviews·M W Peczuh, A D Hamilton
Feb 20, 2002·Chemical Reviews·Pierre Terech, Richard G. Weiss
Aug 29, 2002·Journal of the American Chemical Society·Albertus P H J SchenningE W Meijer
Sep 21, 2002·Chemical Communications : Chem Comm·F WürthnerC Tschierske
Feb 1, 2003·The Journal of Organic Chemistry·Maria ArduiniDavid N Reinhoudt
Mar 4, 2003·Chemical Communications : Chem Comm·Rint P Sijbesma, E W Meijer
Dec 18, 2003·Journal of the American Chemical Society·Pascal JonkheijmE W Meijer
Dec 25, 2003·Angewandte Chemie·Pascal JonkheijmE W Meijer
Mar 11, 2004·Chemical Reviews·Lara A Estroff, Andrew D Hamilton
Jun 5, 2004·Science·Jonathan P HillTakuzo Aida
Jul 21, 2004·Chemical Communications : Chem Comm·Frank Würthner
Sep 17, 2004·Chemistry : a European Journal·Ulf DrechslerVincent M Rotello
Nov 4, 2004·Journal of the American Chemical Society·Benjamin W MessmoreSamuel I Stupp
Jan 6, 2005·Journal of the American Chemical Society·James F HulvatSamuel I Stupp
Jan 6, 2005·Journal of the American Chemical Society·Joaquín BarberáTeresa Sierra
Feb 24, 2005·Chemical Society Reviews·Henk M Keizer, Rint P Sijbesma
Apr 14, 2005·Chemical Reviews·Freek J M HoebenAlbertus P H J Schenning
Sep 21, 2005·Chemical Society Reviews·Neralagatta M Sangeetha, Uday Maitra
Dec 15, 2005·Angewandte Chemie·Takashi KatoKenji Kishimoto
Apr 20, 2006·Journal of the American Chemical Society·Keisuke TajimaSamuel I Stupp
Jul 11, 2006·Science·Pascal JonkheijmE W Meijer
Oct 26, 2006·Journal of the American Chemical Society·Jung-Keun KimMyongsoo Lee
Nov 16, 2006·Journal of the American Chemical Society·Hiroshi NakadeVincent M Rotello
Feb 3, 2007·Organic & Biomolecular Chemistry·Freek J M HoebenE W Meijer
Feb 13, 2007·Chemical Reviews·Jishan WuKlaus Müllen
May 11, 2007·Accounts of Chemical Research·Ayyappanpillai Ajayaghosh, Vakayil K Praveen
Oct 9, 2007·Journal of the American Chemical Society·Shiki YagaiAkihide Kitamura
Jan 17, 2008·Chemical Society Reviews·Ayyappanpillai AjayaghoshChakkooth Vijayakumar
Aug 2, 2008·Chemistry : a European Journal·Freek J M HoebenSteven De Feyter
Sep 20, 2008·Chemical Communications : Chem Comm·Shiki YagaiAkihide Kitamura
Dec 25, 2008·Journal of the American Chemical Society·Anna Llanes-PallasDavide Bonifazi
Mar 27, 2009·Chemical Communications : Chem Comm·Takashi KatoMasafumi Yoshio
Mar 28, 2009·Journal of the American Chemical Society·Shiki YagaiYoshihiro Kikkawa

❮ Previous
Next ❯

Citations

Jun 13, 2015·Chemical Communications : Chem Comm·Qingqing MiaoGaolin Liang
Aug 16, 2017·Chemical Communications : Chem Comm·Bimalendu AdhikariShiki Yagai
Nov 5, 2011·Chemistry : a European Journal·Shiki YagaiYoshihiro Kikkawa
Mar 3, 2011·Chemistry : a European Journal·Tomohiro SekiShiki Yagai
Oct 25, 2013·Chemical Communications : Chem Comm·Sibasish PaulSurajit Sinha
Sep 29, 2011·Chemistry : a European Journal·Bimalendu AdhikariArindam Banerjee
Oct 23, 2012·Chemistry, an Asian Journal·Dibakar Kumar Maiti, Arindam Banerjee
May 2, 2015·Chemistry, an Asian Journal·Kalathil K KarthaAyyappanpillai Ajayaghosh
Feb 16, 2011·Physical Chemistry Chemical Physics : PCCP·Chakkooth VijayakumarAyyappanpillai Ajayaghosh
Apr 23, 2013·Chemical Communications : Chem Comm·Mitsuaki YamauchiShiki Yagai
Apr 19, 2013·Chemistry : a European Journal·Shiki YagaiShinobu Uemura
Mar 29, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Xinhua CaoChunhui Huang
Sep 30, 2017·The Journal of Organic Chemistry·Yoshifumi SasanoHiromitsu Maeda
May 21, 2015·Journal of the American Chemical Society·Luka ĐorđevićDavide Bonifazi
Oct 23, 2012·Journal of the American Chemical Society·Shiki YagaiYoshihiro Kikkawa
Jan 10, 2014·Chemical Reviews·Sukumaran Santhosh BabuAyyappanpillai Ajayaghosh
Nov 20, 2013·Langmuir : the ACS Journal of Surfaces and Colloids·D Sirisha Janni, Muraleedharan K Manheri
Jun 22, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Mingming Ma, Dennis Bong

❮ 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.