NDLI: Expanded Pyridiniums: Bis-cyclization of Branched Pyridiniums into Their Fused Polycyclic and Positively Charged Derivatives—Assessing the Impact of Pericondensation on Structural, Electrochemical, Electronic, and Photophysical Features

Please wait, while we are loading the content...

Year: 2017 Volume: 23

Year: 2016 Volume: 22

Year: 2015 Volume: 21

Year: 2014 Volume: 20

Year: 2013 Volume: 19

Year: 2012 Volume: 18

Year: 2011 Volume: 17

Year: 2010 Volume: 16

Year: 2010 Volume: 16 Issue: 48

Year: 2010 Volume: 16 Issue: 47

Year: 2010 Volume: 16 Issue: 46

Year: 2010 Volume: 16 Issue: 45

Year: 2010 Volume: 16 Issue: 44

Year: 2010 Volume: 16 Issue: 43

Year: 2010 Volume: 16 Issue: 42

Year: 2010 Volume: 16 Issue: 41

Year: 2010 Volume: 16 Issue: 40

Year: 2010 Volume: 16 Issue: 39

Year: 2010 Volume: 16 Issue: 38

Year: 2010 Volume: 16 Issue: 37

Year: 2010 Volume: 16 Issue: 36

Selenium- and Tellurium-Containing Multifunctional Redox Agents as Biochemical Redox Modulators with Selective Cytotoxicity

Pyrene-Based Fluorescent Nitric Oxide Cheletropic Traps (FNOCTs) for the Detection of Nitric Oxide in Cell Cultures and Tissues

AT-Specific DNA Binding of Binuclear Ruthenium Complexes at the Border of Threading Intercalation

Studies on the Reactivity of $[Ge_{9}]^{4−}$ towards $[Fe(cot)(CO)_{3}]:$ Synthesis and Characterization of $[Ge_{8}Fe(CO)_{3}]^{3−}$ and of the Anionic Organometallic Species $[Fe(cot)(CO)_{3}]^{−†}$

Curvularides A–E: Antifungal Hybrid Peptide–Polyketides from the Endophytic Fungus Curvularia geniculata

Azaphenalene Phthalocyanines: Phthalocyanine Analogues with Six-Membered-Ring Units Instead of Five-Membered-Ring Units

Tripodal Thiols as Ligands for Molecular Magnets: Very Strong Antiferromagnetic Exchange Interactions in Vanadium(III) Clusters

Water Stable Zr–Benzenedicarboxylate Metal–Organic Frameworks as Photocatalysts for Hydrogen Generation

Pt–NiCo Nanostructures with Facilitated Electrocatalytic Activities for Sensitive Determination of Intracellular Thiols with Long-Term Stability

Synthesis and Conformational Characterisation of Hexameric β-Peptide Foldamers by Using Double POAC Spin Labelling and $cw-EPR^{†}$

Copper-Catalysed Domino Silylative Aldol Reaction Leading to Stereocontrolled Chiral Quaternary Carbons

New Chiral Calixsalen Chromium Complexes: Recyclable Asymmetric $Catalysts^{†}$

Structural and Electronic Effects of Carbon-Supported $Pt_{x}Pd_{1−x}$ Nanoparticles on the Electrocatalytic Activity of the Oxygen-Reduction Reaction and on Methanol Tolerance

Highly Ordered Mesoporous Cobalt Oxide Nanostructures: Synthesis, Characterisation, Magnetic Properties, and Applications for Electrochemical Energy Devices

Construction of a Novel Topological Frustrated System: A Frustrated Metal Cluster in a Helical Space

ADLOC: An Aptamer-Displacement Assay Based on Luminescent Oxygen Channeling

Gold(I) and Brønsted Acid Catalyzed Intramolecular Rearrangements of Vinylidenecyclopropanes

Isovitamin $B_{12}:$ A Vitamin $B_{12}$ Derivative That Flips Its Tail

Expanded Pyridiniums: Bis-cyclization of Branched Pyridiniums into Their Fused Polycyclic and Positively Charged Derivatives—Assessing the Impact of Pericondensation on Structural, Electrochemical, Electronic, and Photophysical Features

Bufogargarizins A and B: Two Novel 19-Norbufadienolides with Unprecedented Skeletons from the Venom of Bufo bufo gargarizans

A Flow Microreactor System Enables Organolithium Reactions without Protecting Alkoxycarbonyl Groups

Trifluoromethyl-Substituted Conjugated Oligoelectrolytes

The Effect of Ligand Denticity in Size-Selective Synthesis of Calix[n]arene-Stabilized Gold Nanoparticles: A Multitechnique Approach

Chirally Organized Oligothiophenes: Towards Modeling Interchain Interactions Within π-Conjugated Systems

$[Pd(Cl)_{2}\{P(NC_{5}H_{10})(C_{6}H_{11})_{2}\}_{2}]—A$ Highly Effective and Extremely Versatile Palladium-Based Negishi Catalyst that Efficiently and Reliably Operates at Low Catalyst Loadings

Non-innocent Behaviour of Dithiocarboxylate Ligands Based on N-Heterocyclic Carbenes

Palladium(II)-Catalyzed Highly Regio- and Stereoselective Synthesis of 2-Chloro-1,3-diene Derivatives from Alkynols and Alkenes

Scaling out by microwave-assisted, continuous flow organic synthesis (MACOS): multi-gram synthesis of bromo- and fluoro-benzofused sultams benzthiaoxazepine-1,1-dioxides.

Nanographite impurities dominate electrochemistry of carbon nanotubes.

Highly enantioselective Michael addition of malononitrile to vinylogous imine intermediates generated in situ from arylsulfonyl indoles.

Rhodium-Catalysed Intermolecular Alkyne Hydroacylation: The Enantioselective Synthesis of α- and β-Substituted Ketones by Kinetic Resolution

Ionic Mixed Interactions in Macromolecules

Ketone–Alcohol Hydrogen-Transfer Equilibria: Is the Biooxidation of Halohydrins Blocked?

Modulation of the Aerobic Oxidative Polymerization in Phenylazomethine Dendrimers Assembling Copper Complexes

Electronic and Optical Properties in the Solid-State Molecular Assemblies of Anion-Responsive Pyrrole-Based π-Conjugated Systems

Year: 2010 Volume: 16 Issue: 35

Year: 2010 Volume: 16 Issue: 34

Year: 2010 Volume: 16 Issue: 33

Year: 2010 Volume: 16 Issue: 32

Year: 2010 Volume: 16 Issue: 31

Year: 2010 Volume: 16 Issue: 30

Year: 2010 Volume: 16 Issue: 29

Year: 2010 Volume: 16 Issue: 28

Year: 2010 Volume: 16 Issue: 27

Year: 2010 Volume: 16 Issue: 26

Year: 2010 Volume: 16 Issue: 25

Year: 2010 Volume: 16 Issue: 24

Year: 2010 Volume: 16 Issue: 23

Year: 2010 Volume: 16 Issue: 22

Year: 2010 Volume: 16 Issue: 21

Year: 2010 Volume: 16 Issue: 20

Year: 2010 Volume: 16 Issue: 19

Year: 2010 Volume: 16 Issue: 18

Year: 2010 Volume: 16 Issue: 17

Year: 2010 Volume: 16 Issue: 16

Year: 2010 Volume: 16 Issue: 15

Year: 2010 Volume: 16 Issue: 14

Year: 2010 Volume: 16 Issue: 13

Year: 2010 Volume: 16 Issue: 12

Year: 2010 Volume: 16 Issue: 11

Year: 2010 Volume: 16 Issue: 10

Year: 2010 Volume: 16 Issue: 9

Year: 2010 Volume: 16 Issue: 8

Year: 2010 Volume: 16 Issue: 7

Year: 2010 Volume: 16 Issue: 6

Year: 2010 Volume: 16 Issue: 5

Year: 2010 Volume: 16 Issue: 4

Year: 2010 Volume: 16 Issue: 3

Year: 2010 Volume: 16 Issue: 2

Year: 2010 Volume: 16 Issue: 1

Year: 2009 Volume: 15

Year: 2008 Volume: 14

Year: 2007 Volume: 13

Year: 2006 Volume: 12

Year: 2005 Volume: 11

Year: 1997 Volume: 3

Expanded Pyridiniums: Bis-cyclization of Branched Pyridiniums into Their Fused Polycyclic and Positively Charged Derivatives—Assessing the Impact of Pericondensation on Structural, Electrochemical, Electronic, and Photophysical Features

Content Provider	World Health Organization (WHO)-Global Index Medicus
Author	Fortage, Jérôme Ciofini, Ilaria Ochsenbein, Philippe Griveau, Sophie Bedioui, Fethi Puntoriero, Fausto Lainé, Philippe P. Tuyèras, Fabien Nastasi, Francesco Campagna, Sebastiano
Description	Author Affiliation: Fortage J ( Laboratoire de Chimie et Biochimie Pharmacologiques et Toxicologiques (CNRS UMR-8601), Université Paris Descartes, 45, rue des Saints Pères, 75270 Paris Cedex 06, France.)
Abstract	This study evaluates the impact of the extension of the π-conjugated system of pyridiniums on their various properties. The molecular scaffold of aryl-substituted expanded pyridiniums (referred to as branched species) can be photochemically bis-cyclized into the corresponding fused polycyclic derivatives (referred to as pericondensed species). The representative 1,2,4,6-tetraphenylpyridinium $(1^{H})$ and 1,2,3,5,6-pentaphenyl-4-(p-tolyl)pyridinium $(2^{Me})$ tetra- and hexa-branched pyridiniums are herein compared with their corresponding pericondensed derivatives, the fully fused 9-phenylbenzo[1,2]quinolizino[3,4,5,6-def]phenanthridinium $(1^{H}f)$ and the hitherto unknown hemifused 9-methyl-1,2,3-triphenylbenzo[h]phenanthro[9,10,1-def]isoquinolinium $(2^{Me}f).$ Combined solid-state X-ray crystallography and solution NMR experiments showed that stacking interactions are barely efficient when the pericondensed pyridiniums are not appropriately substituted. The electrochemical study revealed that the first reduction process of all the expanded pyridiniums occurs at around −1 V vs. SCE, which indicates that the lowest unoccupied molecular orbital (LUMO) remains essentially localized on the pyridinium core regardless of pericondensation. In contrast, the electronic and photophysical properties are significantly affected on going from branched to pericondensed pyridiniums. Typically, the number of absorption bands increases with extended activity towards the visible region (down to ca. 450 nm in MeCN), whereas emission quantum yields are increased by three orders of magnitude (at ca. 0.25 on average). A relationship is established between the observed differential impact of the pericondensation and the importance of the localized LUMO on the properties considered: predominant for the first reduction process compared with secondary for the optical and photophysical properties.
ISSN	09476539
e-ISSN	15213765
Journal	Chemistry - A European Journal
Issue Number	36
Volume Number	16
Language	English
Publisher	Wiley-VCH;ChemPubSoc Europe
Publisher Date	2010-09-24
Publisher Place	Germany
Access Restriction	Open
Subject Keyword	Polycyclic Compounds Chemistry Pyridinium Compounds Crystallography, X-Ray Cyclization Electrochemistry Magnetic Resonance Spectroscopy Molecular Structure Research Support, Non-U.S. Gov't
Content Type	Text
Resource Type	Article
Subject	Organic Chemistry Catalysis

Central Library (ISO-9001:2015 Certified)
Indian Institute of Technology Kharagpur
Kharagpur, West Bengal, India | PIN - 721302

See location in the Map
03222 282435
Mail: support@ndl.gov.in

Sl.	Authority	Responsibilities	Communication Details
1	Ministry of Education (GoI), Department of Higher Education	Sanctioning Authority	https://www.education.gov.in/ict-initiatives
2	Indian Institute of Technology Kharagpur	Host Institute of the Project: The host institute of the project is responsible for providing infrastructure support and hosting the project	https://www.iitkgp.ac.in
3	National Digital Library of India Office, Indian Institute of Technology Kharagpur	The administrative and infrastructural headquarters of the project	Dr. B. Sutradhar bsutra@ndl.gov.in
4	Project PI / Joint PI	Principal Investigator and Joint Principal Investigators of the project	Dr. B. Sutradhar bsutra@ndl.gov.in Prof. Saswat Chakrabarti will be added soon
5	Website/Portal (Helpdesk)	Queries regarding NDLI and its services	support@ndl.gov.in
6	Contents and Copyright Issues	Queries related to content curation and copyright issues	content@ndl.gov.in
7	National Digital Library of India Club (NDLI Club)	Queries related to NDLI Club formation, support, user awareness program, seminar/symposium, collaboration, social media, promotion, and outreach	clubsupport@ndl.gov.in
8	Digital Preservation Centre (DPC)	Assistance with digitizing and archiving copyright-free printed books	dpc@ndl.gov.in
9	IDR Setup or Support	Queries related to establishment and support of Institutional Digital Repository (IDR) and IDR workshops	idr@ndl.gov.in