31161-46-3Relevant articles and documents
High electron mobility in solution-cast and vapor-deposited phenacyl-quaterthiophene-based field-effect transistors: Toward N-type polythiophenes
Letizia, Joseph A.,Facchetti, Antonio,Stern, Charlotte L.,Ratner, Mark A.,Marks, Tobin J.
, p. 13476 - 13477 (2005)
New carbonyl-functionalized quaterthiophenes, 5,5?-diperfluorophenylcarbonyl-2,2′:5′,2″:5″,2?-quaterthiophene [DFCO-4T], 5,5?-diphenyl-2,2′:5′,2″:5″,2?-quaterthiophene [DPCO-4T], and a polymer having the same basic motif as DFCO-4T, poly{1,4-bis[(3′-n-oct
Aroylation of Electron-Rich Pyrroles under Minisci Reaction Conditions
Laha, Joydev K.,Kaur Hunjan, Mandeep,Hegde, Shalakha,Gupta, Anjali
, p. 1442 - 1447 (2020/02/22)
The development of Minisci acylation on electron-rich pyrroles under silver-free neutral conditions has been reported featuring the regioselective monoacylation of (NH)-free pyrroles. Unlike conventional Minisci conditions, the avoidance of any acid that could result in the polymerization of pyrroles was the key to success. The umpolung reactivity of the nucleophilic acyl radical, generated in situ from arylglyoxylic acid, could help explain the mechanism of product formation with electron-rich pyrroles. Alternatively, the nucleophilic substitution of the acyl radical on the electron-deficient pyrrole radical cation is proposed.
Phenacyl-thiophene and quinone semiconductors designed for solution processability and air-Stability in high mobility n-channel field-effect transistors www.chemeurj.org
Letizia, Joseph A.,Cronin, Scott,Ortiz, Rocio Ponce,Facchetti, Antonio,Ratner, Mark A.,Marks, Tobin J.
scheme or table, p. 1911 - 1928 (2010/06/16)
Electron-transporting organic semiconductors (n-channel) for fieldeffect transistors (FETs) that are processable in common organic solvents or exhibit air-stable operation are rare. This investigation addresses both these challenges through rational molecular design and computational predictions of n-channel (FETs) air-stability. A series of seven phenacyl-thiophene-based materials are reported incorporating systematic variations in molecular structure and reduction potential. These compounds are as follows: 5,5?-bis(perfluorophenylcarbonyl)-2,2′:5′,-2″:5″, 2?-quaterthiophene (1), 5,5?-bis-(phenacyl)-2,2′;5′, 2″: 5″,2?-quaterthiophene (2), poly[5,5?- (perfluorophenac-2-yl)-4′,4″-dioctyl-2,2':5',2":5", 2'"-quaterthiophene) (3), 5,5?-bis(perfluorophenacyl)-4,4?- dioctyl-2,2′:5′,2″:5″,2?-quaterthiophene (4), 2,7-bis((5-perfluorophenacyl)thiophen-2-yl)-9,10phenanthrenequinone (5), 2,7-bis[(5phenacyl)thiophen-2-yl]-9,10-phenanthrenequinone (6), and 2,7-bis(thiophen-2-yl)-9,10-phenanthrenequinone, (7). Optical and electrochemical data reveal that phenacyl functionalization significantly depresses the LUMO energies, and introduction of the quinone fragment results in even greater LUMO stabilization. FET measurements reveal that the films of materials 1, 3, 5, and 6 exhibit n-channel activity. Notably, oligomer 1 exhibits one of the highest, μe (up to ≈0.3 Cm 2V-1S-1) values reported to date for a solutioncast organic semiconductor; one of the first n-channel polymers, 3, exhibits μe ≈ 10-6 Cm2V -1S-1 in spin-cast films (μc = 0.02 cm 2 V-1S-1 for drop-cast 1:3 blend films); and rare air-stable n-channel material 5 exhibits n-channel FET operation with μe = 0.015 cm2V-1s-1, while maintaining a large Ion:off= 106 for a period greater than one year in air. The crystal structures of 1 and 2 reveal close herringbone interplanar π-stacking distances (3.50 and 3.43 A, respectively), whereas the structure of the model quinone compound, 7, exhibits 3.48 A cofacial π-stacking in a slipped, donor-acceptor motif.
