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Synthesis and characterization of novel optically active and photoactive aromatic polyesters containing 1,8-naphthalimidyl pendant group by step-growth polymerization

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Abstract

Novel optically active polyesters (PE)s by step-growth polymerization of a chiral diacid containing naphthalimidyl and flexible chiral groups with different diols via direct polyesterification reaction with tosyl chloride/pyridine/dimethylformamide system as condensing agent were prepared. The resulting PEs were characterized using FT-IR, 1H NMR, UV–vis spectroscopy, fluorimetry, and elemental analysis. Fluorescence properties of the PE3h as a representative one were examined in several polar aprotic solvents which reveal that this polymer has photoactive properties. Furthermore, thermal properties of these polymers were investigated using thermogravimetric and differential thermogravimetric analyses. The glass-transition temperatures of PE3b and PE3f were recorded between 264 and 220 °C by differential scanning calorimetry, and the 10% weight loss temperatures were ranging from 350 °C under nitrogen. The obtained macromolecules are readily soluble in many organic solvents.

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Acknowledgments

We wish to express our gratitude to the Research Affairs Division, Isfahan University of Technology (IUT), for partial financial support. Further financial support from National Elite Foundation (NEF) and Center of Excellency in Sensors and Green Research (IUT) is gratefully acknowledged. We also thanks in advanced Prof. B. Rezaie (Analytical Chemistry Division of IUT), Prof. M. Amirnasr (Inorganic Chemistry Division of IUT), Mr. M. Dinari, Mr. M. Taghavi, and Dr. Z. Rafiee for helpful discussions.

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  1. Organic Polymer Chemistry Research Laboratory, Department of Chemistry, Isfahan University of Technology, Isfahan, 84156-83111, Islamic Republic of Iran

    Shadpour Mallakpour & Elaheh Hashemi

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  1. Shadpour Mallakpour
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  2. Elaheh Hashemi
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Correspondence to Shadpour Mallakpour.

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Mallakpour, S., Hashemi, E. Synthesis and characterization of novel optically active and photoactive aromatic polyesters containing 1,8-naphthalimidyl pendant group by step-growth polymerization. Polym. Bull. 65, 551–563 (2010). https://doi.org/10.1007/s00289-009-0226-9

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  • DOI: https://doi.org/10.1007/s00289-009-0226-9

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