Post-synthetic modification of a macrocyclic receptor via regioselective imidazolium ring-opening

Chemical Science
Jia ShangJonathan L. Sessler

Abstract

A facile post-synthetic modification of a tetracationic tetraimidazolium macrocycle, 14+ (i.e., the "Texas-sized" molecular box (cyclo[2](2,6-di(1H-imidazol-1-yl)pyridine)[2](1,4-dimethylenebenzene)), is described. Under mild basic conditions, ring-opening of the imidazolium moieties occurs. This results in two new isomeric dicationic macrocycles. This simple yet efficient modification serves to alter the size of the molecular cavity, the charge of the macromolecular receptor, and the manner whereby it interacts with dianionic guest molecules. The isomeric mixture of imidazolium ring opened macrocycles can be synthesized in relatively high overall yield (86-93%). The reaction shows regioselectivity and the ratio of major to minor (i.e., trans : cis ring-opened products) was determined to be ca. 3 : 1 via1H NMR spectroscopy. The major isomer, trans-cyclo[2]((Z)-N-(2-((6-(1H-imidazol-1-yl)pyridin-2-yl)amino)vinyl)formamide)[2](1,4-bismethylbenzene) hexafluorophosphate (22+·2PF6-), was isolated in its pure form in 42% yield via recrystallization. The molecular recognition properties of 22+ were investigated using a series of dianionic guests (i.e., 2,6-naphthalenedicarboxylate (4), 2,6-naphthalenedisulfonate (5), and 1,5-naphthale...Continue Reading

References

Apr 25, 2000·Angewandte Chemie·G CafeoD J Williams
Nov 15, 2000·The Journal of Organic Chemistry·P AnzenbacherP A Gale
Feb 19, 2002·Chemical Reviews·Françisco M. Raymo, J. Fraser Stoddart
Jan 16, 2003·Journal of the American Chemical Society·Xuehe LiBruce C Gibb
Nov 13, 2003·Chemistry : a European Journal·Bruce C Gibb
Mar 28, 2006·Chemical Society Reviews·Juyoung YoonKwang S Kim
Mar 28, 2006·Chemical Society Reviews·He Tian, Qiao-Chun Wang
Jul 27, 2006·Journal of the American Chemical Society·David Schultz, Jonathan R Nitschke
Oct 26, 2007·Chemistry : a European Journal·Weidong ZhouDaoben Zhu
Sep 26, 2008·Chemical Communications : Chem Comm·Mei-Xiang Wang
Jan 27, 2009·Chemical Society Reviews·Claudia Caltagirone, Philip A Gale
Apr 23, 2009·Chemical Society Reviews·Zhenqiang Wang, Seth M Cohen
Jun 18, 2009·Organic & Biomolecular Chemistry·Charlotte E WillansJonathan W Steed
Jul 10, 2009·Chemical Society Reviews·J Fraser Stoddart
Jan 9, 2010·Journal of the American Chemical Society·Ting ChenPeter J Stang
Apr 24, 2010·Nature Chemistry·Han-Yuan GongJonathan L Sessler
Aug 26, 2010·Chemical Society Reviews·Sung Kuk Kim, Jonathan L Sessler
Nov 26, 2010·Chemical Society Reviews·Kristine K Tanabe, Seth M Cohen
Dec 23, 2010·Journal of the American Chemical Society·Oldamur HollóczkiLászló Nyulászi
Jan 7, 2011·Journal of the American Chemical Society·Han-Yuan GongJonathan L Sessler
Apr 9, 2011·Chemical Communications : Chem Comm·Emily F V DryJonathan R Nitschke
Sep 1, 2011·Journal of the American Chemical Society·Jeremiah J GassensmithJ Fraser Stoddart
Sep 16, 2011·Angewandte Chemie·Perdita E BarranMichael Zengerle
Jan 19, 2012·Chemical Communications : Chem Comm·Kevin P McDonaldAmar H Flood
Apr 17, 2012·Angewandte Chemie·Victor BlancoBartosz Lewandowski
May 24, 2012·Chemical Society Reviews·Dong-Sheng Guo, Yu Liu
May 24, 2012·Chemical Society Reviews·Xuzhou YanFeihe Huang
Jul 26, 2012·Organic & Biomolecular Chemistry·Nicholas G WhitePaul D Beer
Dec 19, 2012·Journal of the American Chemical Society·De-Xian Wang, Mei-Xiang Wang
Jan 25, 2013·Chemistry : a European Journal·Caroline ClavelFrédéric Coutrot
Feb 1, 2013·Chemistry : a European Journal·Evgeny A KataevVictor N Khrustalev
Aug 27, 2013·Chemical Communications : Chem Comm·Yibao LiQingdao Zeng
Sep 11, 2013·Chemistry : a European Journal·Nissa C FrankStephen J Loeb
Sep 14, 2013·Journal of the American Chemical Society·Yuran HuaAmar H Flood
Feb 25, 2014·Journal of the American Chemical Society·Raghunath O RamabhadranKrishnan Raghavachari
Mar 29, 2014·Accounts of Chemical Research·Dong-Sheng Guo, Yu Liu
Mar 29, 2014·Chemical Society Reviews·Nicholas H Evans, Paul D Beer
Apr 1, 2014·Chemical Society Reviews·Rajesh KumarJong Seung Kim

❮ Previous
Next ❯

Citations

Jan 18, 2020·Chemistry : a European Journal·Sheng TaoNing Liu
Oct 2, 2020·Organic & Biomolecular Chemistry·Stephen M Butler, Katrina A Jolliffe
Aug 3, 2017·Chemical Communications : Chem Comm·Yu-Dong YangHan-Yuan Gong
Dec 12, 2019·The Journal of Organic Chemistry·Agata Tyszka-Gumkowska, Janusz Jurczak
May 15, 2018·Journal of the American Chemical Society·Ren-Tsung WuJonathan L Sessler
Jan 14, 2022·Chemical Reviews·Yue ZhaoYanli Zhao

❮ Previous
Next ❯

Methods Mentioned

BETA
X-ray
NMR
irradiating
single-crystal diffraction

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.