5875-75-2Relevant academic research and scientific papers
Synthesis and properties of novel fluorinated subnaphthalocyanines for organic photovoltaic cells
Takao, Yuko,Masuoka, Tomoaki,Yamamoto, Koji,Mizutani, Tadashi,Matsumoto, Fukashi,Moriwaki, Kazuyuki,Hida, Koichi,Iwai, Toshiyuki,Ito, Takatoshi,Mizuno, Takumi,Ohno, Toshinobu
supporting information, p. 4564 - 4567 (2014/12/11)
Novel fluorinated subnaphthalocyanine derivatives were newly designed and synthesized as donor materials for low molecular organic photovoltaic cells using fullerene as an acceptor. They were designed to have the low-lying HOMO energy levels for improvement of open circuit voltage without any expense of short-circuit current density. The HOMO/LUMO energy levels of hexafluoro-, heptafluoro-, dodecafluoro-, tridecafluoro- and the parent subnaphthalocyanine estimated based on the photoelectron spectroscopy were -5.69/-3.93, -5.67/-3.90, -5.96/-4.19, -5.92/-4.11 and -5.30/-3.58 eV, respectively, showing that frontier orbital energy levels can be effectively tuned by fluorination.
Synthesis and nonlinear optical properties of fluorine-containing naphthalocyanines
Yang, Guo Ying,Hanack, Michael,Lee, Yiew Wang,Chen, Yu,Lee, May Ka Yuen,Dini, Danilo
, p. 2758 - 2762 (2007/10/03)
The fluorine-containing metal naphthalocyanines [F16NcGaCl] (7) and [(F16NcGa)2O] (8), which represent the first examples of peripherally fluorine substituted naphthalocyanines, were synthesized, and the nonlinear optical transmission was studied. Peripheral substitution by fluorine atoms enhances the solubility and photostability of the naphthalocyanines. In particular, for the axially μ-oxo-bridged naphthalocyanine dimer 8, practically no aggregation was observed in organic solvents and it has proved to be an efficient optical limiter when irradiated with laser light pulses at the wavelength of 532 nm, with pulse duration of 5 ns and repetition rate of 20 Hz.
Synthesis of benzonorbornadienes: Regioselective benzyne formation
Caster,Keck,Walls
, p. 2932 - 2936 (2007/10/03)
This report details the synthesis of several benzonorbornadienes by Diels-Alder cycloaddition of cyclopentadiene derivatives with substituted benzyne intermediates, which were generated by low-temperature metal-halogen exchange of halobenzenes. General conditions were developed, allowing synthesis of most benzonorbornadienes described herein at the multigram scale with isolated yields approaching 90% in some cases. Cycloaddition of the benzyne produced by substitution of a chlorodifluorobenzene for a bromodifluorobenzene in the metal-halogen exchange reaction unexpectedly gave a different benzonorbornadiene. The benzyne, which resulted by a deprotonation pathway rather than by metal-halogen exchange, formed in a highly regioselective elimination step.
Preparation and Spectroscopic Studies of the 1,4-Dihydro-1,4-iminonaphthalene (7-Azabenzonorbornadiene) Ring System
Davies, John W.,Durrant, Michael L.,Walker, Matthew P.,Belkacemi, Djaballah,Malpass, John R.
, p. 861 - 884 (2007/10/02)
The synthesis of a range of N-alkyl 1,4-dihydro-1,4-iminonaphthalenes (7-azabenzonorbornadienes) and reduced derivatives is described together with 1,4-dihydro-1,4- and 9,10-dihydro-9,10- iminoanthracenes.VT NMR studies lead to unambiguous assignment of i
