Localization/delocalization of charges in bay-linked perylene bisimides

Chemistry : a European Journal
Wei JiangFabrizia Negri

Abstract

The copper-mediated Ullmann coupling of 1,7-dibromoperylene bisimides afforded structurally perfect singly-linked perylene bisimide (PBI) arrays, whilst the homo-coupling of 1,12-dibromoperylene bisimides gave doubly-linked and triply-linked diperylene bisimides. The interactions of three bay-linked diperylene bisimides that differed in their linkage (singly, doubly, and triply) were investigated in their neutral and reduced forms (mono-anion to tetra-anion). UV/Vis absorption and fluorescence spectroscopy revealed different degrees of interaction, which was explained by exciton coupling and conjugation effects. The electrochemical properties and spectroelectrochemistry also showed quite-different degrees of PBI interactions in the reduced mixed-valence species, which was apparent by the observation of CT bands. The interpretation of the experimental findings was supported by spin-restricted and -unrestricted DFT and time-dependent TD-DFT calculations with the long-range-corrected CAM-B3LYP functional. Accordingly, the degree of interaction in both the neutral and reduced forms of the bay-linked PBIs was qualitatively in the order doubly linked<singly linked < triply linked, owing to the different degrees of twisting and flexib...Continue Reading

References

May 12, 2000·Chemistry : a European Journal·S F Nelsen
Jun 14, 2001·Journal of the American Chemical Society·S F NelsenY Teki
Dec 26, 2001·Chemical Reviews·K D DemadisT J Meyer
Feb 19, 2002·Chemical Reviews·Pingyun Chen, Thomas J. Meyer
May 9, 2002·Chemical Reviews·Jwanro HassanMarc Lemaire
Jul 19, 2002·Chemical Society Reviews·Bruce S BrunschwigNorman Sutin
Aug 9, 2002·Journal of the American Chemical Society·Tamar van der BoomMichael R Wasielewski
Dec 14, 2002·Chemical Communications : Chem Comm·Christopher KohlKlaus Müllen
Apr 14, 2004·Chemistry : a European Journal·Federico CisnettiGian Piero Spada
Jul 21, 2004·Chemical Communications : Chem Comm·Frank Würthner
Feb 11, 2005·Journal of the American Chemical Society·Caihong XuShigehiro Yamaguchi
Jan 21, 2006·Angewandte Chemie·Neil G PschirerKlaus Müllen
Feb 24, 2006·Organic Letters·Wenfeng QiuDaoben Zhu
Mar 24, 2007·Chemical Reviews·Veaceslav CoropceanuJean-Luc Brédas
Apr 20, 2007·The Journal of Physical Chemistry. B·Jean-Pierre LaunayCedric Hortholary
May 18, 2007·Journal of the American Chemical Society·Yanke CheLing Zang
Aug 19, 2007·Journal of the American Chemical Society·Hualei QianDaoben Zhu
Feb 6, 2008·The Journal of Chemical Physics·Michael J G PeachDavid J Tozer
May 16, 2008·Journal of the American Chemical Society·Yonggang WuZhishan Bo
Aug 14, 2008·Accounts of Chemical Research·Dawei Ma, Qian Cai
Nov 28, 2008·Journal of the American Chemical Society·Hualei QianZhaohui Wang
Jul 18, 2009·Organic Letters·Qifan Yan, Dahui Zhao
Aug 15, 2009·Angewandte Chemie·Florian Monnier, Marc Taillefer
Oct 17, 2009·Journal of the American Chemical Society·Manuel RenzMartin Kaupp
Nov 7, 2009·Journal of the American Chemical Society·Tanmoy DuttaJohannes Gierschner
Dec 17, 2009·Organic Letters·Wei JiangZhaohui Wang
Mar 4, 2010·Chemical Communications : Chem Comm·Yonggang ZhenZhaohui Wang
Apr 9, 2010·The Journal of Physical Chemistry. B·Eugenio Di DonatoFabrizia Negri
Jul 27, 2010·Chemical Communications : Chem Comm·Yonggang ZhenZhaohui Wang

❮ Previous
Next ❯

Citations

Oct 21, 2015·ACS Applied Materials & Interfaces·Ranbir SinghPanagiotis E Keivanidis
Dec 15, 2016·Journal of the American Chemical Society·Conerd K FredericksonMichael M Haley
Sep 13, 2014·Chemical Communications : Chem Comm·Wei SongMeiran Xie
Sep 30, 2014·Accounts of Chemical Research·Wei JiangZhaohui Wang
Jan 26, 2016·Physical Chemistry Chemical Physics : PCCP·Bernard PagoagaGlauco Ponterini
Jun 19, 2018·Chemistry, an Asian Journal·Jianhua ChenXugang Guo
Mar 1, 2019·Photochemical & Photobiological Sciences : Official Journal of the European Photochemistry Association and the European Society for Photobiology·Sofia CanolaFabrizia Negri
Mar 21, 2019·Chemistry : a European Journal·Jungkweon ChoiTetsuro Majima
Dec 7, 2013·Chemical Communications : Chem Comm·Wei JiangZhaohui Wang
Jul 19, 2012·Advanced Materials·Felix SchlosserFrank Würthner
Dec 19, 2012·Chemical Communications : Chem Comm·Hailong WangJianzhuang Jiang
Nov 17, 2017·Chemistry, an Asian Journal·Jiajing FengZhaohui Wang
Apr 25, 2019·Chemical Science·Lixu YangNeil R Champness
Feb 1, 2014·Physical Chemistry Chemical Physics : PCCP·Rocco P Fornari, Alessandro Troisi
Oct 24, 2017·Journal of the American Chemical Society·Guangpeng GaoZhaohui Wang
Nov 18, 2017·ACS Nano·Yasunari TamaiS Matthew Menke
Jul 18, 2014·Organic Letters·Ruchika MishraJeyaraman Sankar
Dec 30, 2017·The Journal of Organic Chemistry·Masaki TakahashiHidemi Yoda
Aug 7, 2021·Chemistry : a European Journal·Seiichiro IzawaMasaki Takahashi

❮ 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.