Synthesis and characterization of a highly strained donor-acceptor nanohoop

Organic & Biomolecular Chemistry
J M Van RadenR Jasti

Abstract

A highly-strained, nitrogen-doped cycloparaphenylene (CPP), aza[6]CPP, was synthesized and then converted to a donor-acceptor nanohoop, N-methylaza[6]CPP, via alkylation of the nitrogen center. The energy levels of the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO) for both molecules were then probed by cyclic voltammetry (CV), which revealed that the donor-acceptor nanohoop had a significantly lower LUMO energy relative to [6]CPP and aza[6]CPP. Density functional theory (DFT) revealed that the donor-acceptor nanohoop underwent a redistribution of the frontier molecular orbital (FMO) density such that a significant portion of the LUMO density resided upon the electron-deficient nitrogen-containing ring. This localization of LUMO density caused a large lowering in the LUMO energy of nearly a full electron volt, while the HOMO energy was less affected due to a large centralization of the FMO on the electron-rich phenylene backbone. This ultimately resulted in a net lowering of the HOMO-LUMO energy gap which was observed both experimentally and computationally. In addition, N-methylaza[6]CPP has a significantly lower energy LUMO than N-methylaza[8]CPP, illustrating that the FMO levels ...Continue Reading

References

Dec 26, 2001·Chemical Reviews·D T McQuadeT M Swager
Dec 15, 2006·Chemical Reviews·John E Anthony
Dec 6, 2008·Journal of the American Chemical Society·Ramesh JastiCarolyn R Bertozzi
Apr 21, 2010·Organic Letters·Yasutomo SegawaKenichiro Itami
Mar 4, 2011·Angewandte Chemie·Yasutomo SegawaKenichiro Itami
May 6, 2011·Journal of the American Chemical Society·Takahiro IwamotoShigeru Yamago
Jan 31, 2012·Angewandte Chemie·Jianlong Xia, Ramesh Jasti
Mar 24, 2012·Organic & Biomolecular Chemistry·Yasutomo SegawaKenichiro Itami
Feb 18, 2015·Accounts of Chemical Research·Matthew R Golder, Ramesh Jasti
Mar 5, 2015·Chemical Society Reviews·Simon E Lewis
Apr 29, 2015·Chemical Society Reviews·Evan R Darzi, Ramesh Jasti
Aug 1, 2015·Journal of the American Chemical Society·Melissa BallColin Nuckolls
May 11, 2016·ACS Central Science·Evan R DarziRamesh Jasti
May 11, 2016·ACS Central Science·Melissa Ball, Colin Nuckolls

❮ Previous
Next ❯

Citations

Sep 27, 2016·Journal of the American Chemical Society·Melissa BallColin Nuckolls
Apr 13, 2017·Chemistry : a European Journal·Shuhei NishigakiKen Tanaka
Jul 21, 2020·Organic & Biomolecular Chemistry·Carlos Augusto Cabral KramerLuciene Santos de Carvalho
Jan 15, 2019·Physical Chemistry Chemical Physics : PCCP·Sofia CanolaFabrizia Negri
Feb 29, 2020·Chemical Science·Melissa L BallMichael L Steigerwald
Feb 17, 2018·Physical Chemistry Chemical Physics : PCCP·Ángel Vidal VidalOlalla Nieto Faza
May 18, 2018·Nature Communications·Boyuan ZhangColin Nuckolls
Sep 10, 2020·Angewandte Chemie·Mathias HermannBirgit Esser
Feb 27, 2021·Angewandte Chemie·Yong YangMichal Juríček
Mar 30, 2021·Chemistry : a European Journal·Saber MirzaeiRaúl Hernández Sánchez
Sep 14, 2018·Organic Letters·Sigma HashimotoShigeru Yamago
Mar 15, 2019·Accounts of Chemical Research·Melissa BallColin Nuckolls
Aug 1, 2018·Journal of the American Chemical Society·Melissa L BallColin Nuckolls
Oct 3, 2018·ACS Central Science·Brittany M WhiteRamesh Jasti
Dec 17, 2020·The Journal of Physical Chemistry Letters·Beatriz Rodríguez-HernándezSebastian Fernandez-Alberti
Apr 14, 2020·The Journal of Physical Chemistry. a·M MoralJ C Sancho-García
Oct 30, 2021·Accounts of Chemical Research·Jinyi WangPingwu Du

❮ 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.