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Debnath, Dipen
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article
Synthesis and optical properties of biphenylene ethynylene co-polymers and their model compounds
Abstract
<p>A new series of biphenylene ethynylene co-polymers, poly(2,5-dialkoxy-4-phenyleneethynylene-4,4-biphenyleneethynylene)s of the general formula [-C ≡C-4-C<sub>6</sub>H<sub>4</sub>-C<sub>6</sub>H<sub>4</sub>-4-C ≡C-C<sub>6</sub>H<sub>2</sub>(2,5-OR)<sub>2</sub>-]<sub>n</sub> (R = C<sub>4</sub>H<sub>9</sub><strong class="EmphasisTypeBold">P1</strong>, C<sub>8</sub>H<sub>17</sub><strong class="EmphasisTypeBold">P2</strong>) has been synthesized using a palladium/copper catalyzed coupling reaction between HC ≡C-4-C<sub>6</sub>H<sub>4</sub>-C<sub>6</sub>H<sub>4</sub>-4-C ≡C-H and IC<sub>6</sub>H<sub>2</sub>(2,5-OR)<sub>2</sub>I. The new co-polymer [-C ≡C-C<sub>6</sub>H<sub>2</sub>(2,5-OC<sub>8</sub>H<sub>17</sub>)<sub>2</sub>-C ≡C-C<sub>6</sub>H<sub>2</sub>(2,5-OC<sub>4</sub>H<sub>9</sub>)<sub>2</sub>-]<sub>n</sub><strong class="EmphasisTypeBold">P5</strong> has also been formed where different alkoxy substituents are present on alternate arene rings in the same polymer backbone. All the polymers were characterized by IR, <sup>1</sup>H and <sup>13</sup>C NMR spectroscopy and by GPC. The model compounds C<sub>6</sub>H<sub>5</sub>-4-C<sub>6</sub>H<sub>4</sub>-C≡C-C<sub>6</sub>H<sub>2</sub>(2,5-OR)<sub>2</sub>-4-C<sub>6</sub>H<sub>4</sub>-C<sub>6</sub>H<sub>5</sub> (R = C<sub>4</sub>H<sub>9</sub><strong class="EmphasisTypeBold">M1</strong>, C<sub>8</sub>H<sub>17</sub><strong class="EmphasisTypeBold">M2</strong>) have also been prepared by the reaction between C<sub>6</sub>H<sub>5</sub>-4-C<sub>6</sub>H<sub>4</sub>-C≡CH and IC<sub>6</sub>H<sub>2</sub>(2,5-OR)<sub>2</sub>I. Single crystal X-ray structures of <strong class="EmphasisTypeBold">M1</strong>, <strong class="EmphasisTypeBold">M2</strong> and Me<sub>3</sub>Si-C≡C-4-C<sub>6</sub>H<sub>4</sub>-C<sub>6</sub>H<sub>4</sub>-4-C≡C-SiMe<sub>3</sub> were determined with a view to obtain a better understanding of the molecular and intermolecular interactions in the solid state which has been used to explain the optical properties of the polymers derived from them. The absorption and photoluminescence spectra of the polymers, <strong class="EmphasisTypeBold">P1</strong>, <strong class="EmphasisTypeBold">P2</strong> and <strong class="EmphasisTypeBold">P5</strong> showed that the lowest energy band is blue shifted due to the introduction of biphenylene fragments into the alkoxy substituted poly(ethynylenephenylene)s.</p>