US EPA

1467888 

Journal Article 

Acenaphtho[1, 2-c]phosphole P-oxide: a phosphole-naphthalene pi-conjugated system with high electron mobility 

Saito, A; Miyajima, T; Nakashima, M; Fukushima, T; Kaji, H; Matano, Y; Imahori, H 

2009 

Yes 

Chemistry: A European Journal
ISSN: 0947-6539
EISSN: 1521-3765 

15 

39 

10000-10004 

English 

19711389 

10.1002/chem.200901378 

WOS:000270854200007 

http://://WOS:000270854200007
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The first comparative study on the optical and electrochemical properties of naphthalene, acenaphthene, and acenaphthylene fused phosphole derivatives, was reported. Naphthalene-, acenaphthene-, and acenaphthylene-fused phosphole derivatives 3-5 were successfully prepared by utilizing a TiII- mediated cyclization of dialkynylated naphthalene (2a), acenaphthene (2b), and acenaphthylene (2c). Treatment of gold(I) complexes 3b,c with excess P(NMe 2)3 afforded o3-P compounds 4b,c, which were subsequently oxidized by m-chloroperbenzoic acid (mCPBA) to the corresponding P-oxides 5b, c. At the last stage of this study, the electron mobility of vacuum-deposited films of 5a and 5b was studied by the time-of-flight (TOF) technique. The results demonstrate that the fusion of the naphthalene ring into the phosphole platform is a highly promising protocol to the development of a new class of phosphole based p-systems with high electron-transporting ability.