The objective of this work was the preparation of a water-soluble conjugated material. Accordingly, 2-amino-(1,4-distyrylbenzene) was synthesized from the reduction of 2-nitro-(1,4-distyrylbenzene), which was prepared via the Wittig-Horner reaction. The novel amino-DSB derivative was soluble in various organic solvents like DMSO, THF, methanol, and acetonitrile. More importantly, the amino-DSB derivative was soluble in water upon protonation with trichloroacetic acid and in neutral aqueous solutions containing 20 % acetonitrile. The new material was characterized by FTIR, 1H-NMR, GC-MS, XRD, and by its absorption and emission profiles. The THF solution of the amino-DSB displayed a UV absorption maximum of 330 nm and an emission maximum of 455 nm. To the best of our knowledge, this is the first DSB derivative containing the amino (NH2) group reported in the literature, even though there are several examples of DSBs containing alkyl-amino groups. The synthetic techniques used in the synthesis of the amino-DSB are currently being explored in the synthesis of water-soluble conjugated polymers containing the amino moiety. Figure 1. <img src='https://acs-archive-assets2.s3.amazonaws.com/240nm/uploads/46222_rc_boston_acs.jpg' alt='' />

Synthesis of a water-soluble distyrylbenezene derivative

247th National Meeting (2014)

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