Synthesis of Compounds for Los Alamos National Laboratory

Abstract

As part of contract 6709U0015-3C, the compounds listed were synthesized and transferred to LANL for evaluation. Work on these has resulted in several papers, manuscripts and talks bearing LANL and UTD co-authorship. The detailed synthetic procedures are described and the chemical structure of the mentioned compounds are shown in a table. Synthetic procedures: (1) 2-Methoxy-5-(2{prime}-ethyl hexyloxy)-1,4-distyrylbenzene--see synthesis of compound V in the reference [1]. (2) MEHPPV : 1.000 g 1,4-methoxyethylhexyloxy-2,5-dibromomethylbenzene + 0.0042 g (1 mol %) anthracene were dissolved in 35 ml dry THF and 1.0 M solution of t-BuOK in THF was added slowly during 60 min and stirred at room temperature for 20 hours. The red suspension was precipitated in 200 ml cold MeOH, the solid was filtered, washed by MeOH and dried in vacuum. The red-orange solid was extracted by boiling hexane for 24 hours. Insoluble in hexane red polymer was extracted by boiling xylene for 24 hours, soluble in xylene fraction was dissolved in THF and precipitated in MeOH. After filtration and drying in vacuum 0.220 g(36% yield) of red polymer with M{sub W}=357000 and absorption maximum at 496 nm (chloroform) was obtained. (3)1,4-distyrylbenzene - see synthesis of compound 1 in the reference [1]. (4)1,4-Bis-(2{prime},5{prime}-dimethoxystyryl)-2-methoxy-5-(2{prime}-ethylhexyloxy)benzene: This compound was obtained in 51% yield according the general procedure for the Wittig reaction described in the reference [1] from 2- methoxy-5(2{prime}-ethylhexyloxy)-1,4-xylylene-bis(triphenylphosphonium chloride) and 2,5-dimethoxybenzaldehyde, m.p.49-51 C. (5) Films of aromatic copolyamides with fragments of 9,10-bis(p-carboxyphenyl) anthracene and bis(m-aminophenyl)-9,10-anthracene--see synthesis of copolyamides XXI and XXII in the reference [2]. (6,7) Films of the solid solution of 9,10-diphenylanthracene in poly(m- phenyleneisophtalamide) (PMPI) were obtained from the 5.0% solution of mixture 0.231 g PMPI and 0.0319 g 9.10-diphenylanthracene in N-MP at conditions described in the reference [2]. (8) 2,5-Didodecyloxy-1,4-distyrylbenzene--see synthesis of compound IV in the reference [1]. (9) 2,5- Dioctyloxy-1,4-distyrylbenzene--see synthesis of compound Ill in the reference [1]. (10) 2,5-Dimethoxy-1,4-distyrylbenzene--see synthesis of compound II in the reference [1]. (11) Films with the compositions of polystyrene (PS) + 2,5-didodecyloxy-1,4- distyrylbenzene (8) (40:60 w/w) and PS + 2,5-dioctyloxy-1,4- distyrylbenzene (9) (40:60 w/w) were obtained by evaporation of 10% solution of components in chloroform at room temperature. (12) FATs and other {omega}-substituted alkane thiols including -CN, -CHO, -OH, -NH{sub 2}.