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Influence of Donor-Acceptor Conjugation Between Thiophene-Phthalazinone Structures Containing Sp(3) C-N Bond on the Frontier Orbital Levels and Optic-Electronic Properties

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Indexed by:期刊论文

Date of Publication:2016-11-01

Journal:JOURNAL OF POLYMER SCIENCE PART A-POLYMER CHEMISTRY

Included Journals:SCIE、EI、Scopus

Volume:54

Issue:21

Page Number:3470-3483

ISSN No.:0887-624X

Key Words:classical aromatic nucleophilic displacement polymerization; phthalazinone; thiophene; UV-vis spectroscopy; thermal properties; structure-property relations

Abstract:Herein, an electron-deficient phthalazinone unit containing a unique Sp(3) hybrid nitrogen atom as an acceptor to cut off the ether bond was presented and three Donor-Acceptor (D-A) conjugated fluoropolymers via Classical Aromatic Nucleophilic Displacement Polymerization (CANDP) method were successfully synthesized. These polymers exhibit excellent thermostability. The 5% weight loss temperature of PDT2TF under nitrogen atmosphere is high, up to 470 degrees C. This is due to that the D-A conjugation between thiophenephthalazinone units affects its resonance energy and stabilizes the thiophene-phthalazinone structures. These three fluoropolymers show strong absorptions and fluorescence in visible light region both in solution and thin film states. The band gaps (E-g) of these polymers are narrower than that of their corresponding di-NH capped monomers, owing to the good electronic communication properties of the Sp(3) nitrogen atom in the phthalazinone unit. The E-g value of PDT3TF is decreased to 2.03 eV. These results indicate that phthalazinone unit is an efficient acceptor and could exhibit strong D-A effect with thiophene unit. Also, the Sp(3) nitrogen atom in the phthalazinone shows good electronic wave function and charge transport properties. This facile CANDP synthetic method combined with Sp(3) C-N bond linked electron-deficient phthalazinone unit affords polymers with controllable photoelectric properties. (C) 2016 Wiley Periodicals, Inc.

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