76727-14-5Relevant academic research and scientific papers
Exciton Isolation in Cross-Pentacene Architecture
Lijina,Benny, Alfy,Ramakrishnan, Remya,Nair, Nanditha G.,Hariharan, Mahesh
supporting information, p. 17393 - 17402 (2020/11/12)
Null aggregates are an elusive, emergent class of molecular assembly categorized as spectroscopically uncoupled molecules. Orthogonally stacked chromophoric arrays are considered as a highlighted architecture for null aggregates. Herein, we unveil the nul
Substituent effects in pentacenes: Gaining control over HOMO-LUMO gaps and photooxidative resistances
Kaur, Irvinder,Jia, Wenling,Kopreski, Ryan P.,Selvarasah, Selvapraba,Dokmeci, Mehmet R.,Pramanik, Chandrani,McGruer, Nicol E.,Miller, Glen P.
supporting information; scheme or table, p. 16274 - 16286 (2009/05/08)
A combined experimental and computational study of a series of substituted pentacenes including halogenated, phenylated, silylethynylated and thiolated derivatives is presented. Experimental studies include the synthesis and characterization of six new and six known pentacene derivatives and a kinetic study of each derivative under identical photooxidative conditions. Structures, HOMO-LUMO energies and associated gaps were calculated at the B3LYP/6-311+G**//PM3 level while optical and electrochemical HOMO-LUMO gaps were measured experimentally. The combined results provide for the first time a quantitative assessment of HOMO-LUMO gaps and photooxidative resistances for a large series of pentacene derivatives as a function of substituents. The persistence of each pentacene derivative is impacted by a combination of steric resistance and electronic effects as well as the positional location of each substituent. Silylethynyl-substituted pentacenes like TIPS-pentacene possess small HOMO-LUMO gaps but are not the longest lived species under photooxidative conditions, contrary to popular perception. A pentacene derivative with both chlorine substituents in the 2,3,9,10 positions and o-alkylphenyl substituents in the 6,13 positions is longer lived than TIPS-pentacene. Of all the derivatives studied, alkylthio- and arylthio-substituted pentacenes are most resistant to photooxidation, possess relatively small HOMO-LUMO gaps and are highly soluble in a variety of organic solvents. These results have broad implications for the field of organic molecular electronics where OFET, OLED, and other applications can benefit from highly persistent, solution processable pentacene derivatives.
Photooxidation and reproduction of pentacene derivatives substituted by aromatic groups
Ono, Katsuhiko,Totani, Hiroaki,Hiei, Takao,Yoshino, Akihiro,Saito, Katsuhiro,Eguchi, Katsuya,Tomura, Masaaki,Nishida, Jun-ichi,Yamashita, Yoshiro
, p. 9699 - 9704 (2008/02/12)
Pentacene derivatives substituted by aromatic groups at the 6,13-positions were prepared and investigated for their electronic properties and the photoaddition reaction with oxygen. The pentacene derivatives substituted by 2-thienyl and phenyl groups reac
Luminescent properties of pentacene derivatives with naphthalene moiety
Kim, Yeong-Eun,Park, Jong-Wook
, p. 137 - 143 (2007/10/03)
Pentacene moiety in electro-optical device which includes solar cell and organic light-emitting diodes (OLEDs) has attracted lots of interest because of its high carrier mobility and dopant property. We synthesized new conjugated compounds, 6,13-diphenylp
Organization of acenes with a cruciform assembly motif
Miao, Qian,Chi, Xiaoliu,Xiao, Shengxiong,Zeis, Roswitha,Lefenfeld, Michael,Siegrist, Theo,Steigerwald, Michael L.,Nuckolls, Colin
, p. 1340 - 1345 (2007/10/03)
This study explores the assembly in the crystalline state of a class of pentacenes that are substituted along their long edges with aromatic rings forming rigid, cruciform molecules. The crystals were grown from the gas phase, and their structures were co
TRANSFORMATIONS THERMIQUES DES PHOTOOXYDES MESO DES ACENES-VI. CAS DES PHOTOOXYDES DE PENTACENES
Sparfel, D.,Gobert, F.,Rigaudy, J.
, p. 2225 - 2235 (2007/10/02)
Thermolysis of the meso-pentacenic photooxides 1P, 1dP and 1tP, in solution, brings about various isomerizations which appear strongly affected by the phenyl substituents.Thus the pentacene photooxide 1P gives only the bicyclic acetal 9P, beside pentacenequinone 5P in high ratio.With the photooxides 1dP of 6,13-diphenylpentacene and 1tP of 5,7,12,14-tetraphenylpentacene, the main products are the naphthocyclobutenic diethers 8dP and 8tP, which are formed in competition with the bicyclic acetals 9dP and 9tP and, in the first case, with an isomer of a new kind, the bis-naphthofuranic diether 13dP.These discrepancies are interpreted in terms of the effect of phenyl groups on the successive steps of the previously established isomerization process of meso-acenic photooxides. Comparative analysis of the chemical shifts of the central carbon atoms, in (13)C NMR, allows the unambiguous assignment of the structure of each isomer.
