PERFORM Publications

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Title		Authors	PubMed ID
1	Regioselective Stepwise Synthesis of Unsymmetrical 1,2,5-Triarylpyrroles via Palladium-Catalyzed Decarboxylative Cross-Coupling and C-H Arylation	Buonomano C; Patterson S; Ngou JS; Messina C; Taylor S; Bilodeau F; Forgione P;	41900086 CHEMBIOCHEM
2	A Modular and Regioselective Synthesis of Di- and Triarylated Thiophenes: Strategies for Accessing Challenging Isomeric Motifs	Messina C; McKibbon K; Wong KS; Prevost P; Petkov V; Forgione P;	41160050 CONCORDIA
3	In vitro evaluation of isatin-pyridine oxime hybrids as potential acetylcholinesterase inhibitors for nerve agent prophylaxis	Silva MCJD; Pinto AMV; Balthar MA; Correa ABA; Bhattacharyya D; Simas ABC; Kuca K; Forgione P; França TCC; Cavalcante SFA; Kitagawa DAS;	40516590 CHEMBIOCHEM
4	A Modular and Catalytic Methodology To Access 2,5-Furan-Based Phenylene/Thiophene Oligomers through a One-Pot Decarboxylative Cross-Coupling from 5-Bromofurfural	Cigana B; Lapointe V; Majewski MB; Forgione P;	38808994 CHEMBIOCHEM
5	Sterically-Hindered Molecular p-Dopants Promote Integer Charge Transfer in Organic Semiconductors	Charoughchi S; Liu JT; Berteau-Rainville M; Hase H; Askari MS; Bhagat S; Forgione P; Salzmann I;	37220083 CHEMBIOCHEM
6	Diverse Applications of Biomass-Derived 5-Hydroxymethylfurfural and Derivatives as Renewable Starting Materials	Chacón-Huete F; Messina C; Cigana B; Forgione P;	35652539 CHEMBIOCHEM
7	Solvent-free synthesis of 3,5-isoxazoles via 1,3-dipolar cycloaddition of terminal alkynes and hydroxyimidoyl chlorides over Cu/Al2O3 surface under ball-milling conditions	Hernandez R RA; Burchell-Reyes K; Braga APCA; Lopez JK; Forgione P;	35424611 CHEMBIOCHEM
8	Characterization of a recently synthesized microtubule-targeting compound that disrupts mitotic spindle poles in human cells	Jaunky DB; Larocque K; Husser MC; Liu JT; Forgione P; Piekny A;	34880347 BIOLOGY
9	Programmed Synthesis of Tetra-Aryl Thiophenes with Stepwise, Ester-Controlled Regioselectivity	Messina C; Ottenwaelder X; Forgione P;	34506149 CHEMBIOCHEM
10	Design, structure-activity relationship study and biological evaluation of the thieno[3,2-c]isoquinoline scaffold as a potential anti-cancer agent	Liu JT; Jaunky DB; Larocque K; Chen F; Mckibbon K; Sirouspour M; Taylor S; Shafeii A; Campbell D; Braga H; Piekny A; Forgione P;	34416378 BIOLOGY
11	Synthesis of 2,5-Diaryl Nonsymmetric Furans C6-Platform Chemicals via Catalytic Conversion of Biomass and the Formal Synthesis of Dantrolene.	Chacón-Huete F, Lasso JD, Szavay P, Covone J, Forgione P	33253575 CHEMBIOCHEM
12	Approaching the Integer-Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross-Coupling	Liu JT; Hase H; Taylor S; Salzmann I; Forgione P;	31961982 CHEMBIOCHEM
13	Facile Aqueous-Phase Synthesis of an Ultrasmall Bismuth Nanocatalyst for the Reduction of 4-Nitrophenol.	Liang Y, Manioudakis J, Macairan JR, Askari MS, Forgione P, Naccache R	31552336 CHEMBIOCHEM
14	Virtual screening, docking, and dynamics of potential new inhibitors of dihydrofolate reductase from Yersinia pestis.	Bastos Lda C, de Souza FR, Guimarães AP, Sirouspour M, Cuya Guizado TR, Forgione P, Ramalho TC, França TC	26494420 CHEMISTRY
15	Analysis of Coxiela burnetti dihydrofolate reductase via in silico docking with inhibitors and molecular dynamics simulation.	de Souza FR, Guimarães AP, Cuya T, de Freitas MP, Gonçalves ADS, Forgione P, Costa França TC	27726597 CHEMBIOCHEM
16	Investigating the selectivity of potential new inhibitors of dihydrofolate reductase from Yersinia pestis designed by molecular modeling.	Bastos LDC, de Souza FR, Pereira Souza LM, Forgione P, Cuya T, de Alencastro RB, Pimentel AS, Celmar Costa França T	29542379 CHEMBIOCHEM

Title:	Approaching the Integer-Charge Transfer Regime in Molecularly Doped Oligothiophenes by Efficient Decarboxylative Cross-Coupling
Authors:	Liu JT, Hase H, Taylor S, Salzmann I, Forgione P
Link:	https://pubmed.ncbi.nlm.nih.gov/31961982/
DOI:	10.1002/anie.201914458
Publication:	Angewandte Chemie (International ed. in English)
Keywords:	charge transfer; decarboxylative cross-coupling; doping; oligothiophenes; organic semiconductors;
PMID:	31961982	Category:	Angew Chem Int Ed Engl	Date Added:	2020-01-22
Dept Affiliation:	CHEMBIOCHEM 1 Department of Chemistry and Biochemistry, Concordia University, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada. 2 Department of Physics, Concordia University, 7141 rue Sherbrooke O., Montréal, QC, H4B 1R6, Canada. 3 Centre for Research in Molecular Modeling (CERMM), Centre for NanoScience Research (CeNSR), Concordia University, 7141 rue Sherbrooke O., Montreal, QC, H4B 1R6, Canada. 4 Center for Green Chemistry and Catalysis, McGill University, 801 rue Sherbrooke O., Montréal, QC, H3A 0B8, Canada.

Description:

A library of symmetrical linear oligothiophene was prepared employing decarboxylative cross-coupling reaction as the key transformation. Thiophene potassium carboxylate salts were used as cross-coupling partners without the need of co-catalyst, base, or additives. This method demonstrates complete chemoselectivity and is a comprehensive greener approach compared to the existing methods. The modularity of this approach is demonstrated with the preparation of discreet oligothiophenes with up to 10 thiophene repeat units. Symmetrical oligothiophenes are prototypical organic semiconductors where their molecular electrical doping as a function of the chain length can be assessed spectroscopically. An oligothiophene critical length for integer charge transfer was observed to be 10 thiophene units, highlighting the potential use of discrete oligothiophenes as doped conduction or injection layers in organic electronics applications.

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