Poly(9,9-dihexylfluorene) derivatives containing electron-transporting aromatic triazole segments: Synthesis, optical and electrochemical properties

Shinn Horng Chen, Chuen Shiou Shiau, Lin Ren Tsai, Yun Chen

Research output: Contribution to journalArticle

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Abstract

We prepared three new poly(9,9-dihexylfluorene) derivatives (P1-P3) containing kinked aromatic triazole (triphenyl-1,2,4-triazole derivative) via Suzuki coupling polymerization. These copolymers were soluble in common organic solvents and showed high decomposition temperatures (Td = 416-454 °C). The optical and electrochemical properties of P1-P3 were compared with poly(9,9-dihexylfluorene) (PFO) and P4 and P5 in which the linkages of the aromatic triazole were different. After introducing the triazole units, absorption spectra showed blue shift (388 nm → 372 nm) due to reduced conjugation, but PL spectra remained almost unchanged (417-418 nm). The linkages of triazole with fluorene segments in P1-P5 were different: (1) fluorene segments linked with triazole through a kinked angle (P1 and P2), (2) triazole as a branch unit (P3) and as terminal groups (P4), (3) fluorene segments linked with triazole in a linear way (P5). As estimated from semi-empirical MNDO calculation, two twisted conformations (ca. 90° each) exist between triazole core and fluorene groups. These kinked conformation and twisted structure increased the PL efficiency (ΦPL = 0.60-0.73, ΦPL = 0.58 for PFO) and partially inhibited annealing-induced excimer formation. From cyclic voltammetric results, P1-P3 exhibited better electron affinity (LUMO: -2.75 to -2.82 eV) than PFO (LUMO: -2.52 eV).

Original languageEnglish
Pages (from-to)8436-8443
Number of pages8
Journalpolymer
Volume47
Issue number26
DOIs
Publication statusPublished - 2006 Dec 8

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Triazoles
Electrochemical properties
Conformations
Optical properties
Derivatives
Electron affinity
Electrons
Organic solvents
Absorption spectra
Copolymers
Polymerization
Annealing
Decomposition
Temperature
fluorene

All Science Journal Classification (ASJC) codes

  • Organic Chemistry
  • Polymers and Plastics

Cite this

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title = "Poly(9,9-dihexylfluorene) derivatives containing electron-transporting aromatic triazole segments: Synthesis, optical and electrochemical properties",
abstract = "We prepared three new poly(9,9-dihexylfluorene) derivatives (P1-P3) containing kinked aromatic triazole (triphenyl-1,2,4-triazole derivative) via Suzuki coupling polymerization. These copolymers were soluble in common organic solvents and showed high decomposition temperatures (Td = 416-454 °C). The optical and electrochemical properties of P1-P3 were compared with poly(9,9-dihexylfluorene) (PFO) and P4 and P5 in which the linkages of the aromatic triazole were different. After introducing the triazole units, absorption spectra showed blue shift (388 nm → 372 nm) due to reduced conjugation, but PL spectra remained almost unchanged (417-418 nm). The linkages of triazole with fluorene segments in P1-P5 were different: (1) fluorene segments linked with triazole through a kinked angle (P1 and P2), (2) triazole as a branch unit (P3) and as terminal groups (P4), (3) fluorene segments linked with triazole in a linear way (P5). As estimated from semi-empirical MNDO calculation, two twisted conformations (ca. 90° each) exist between triazole core and fluorene groups. These kinked conformation and twisted structure increased the PL efficiency (ΦPL = 0.60-0.73, ΦPL = 0.58 for PFO) and partially inhibited annealing-induced excimer formation. From cyclic voltammetric results, P1-P3 exhibited better electron affinity (LUMO: -2.75 to -2.82 eV) than PFO (LUMO: -2.52 eV).",
author = "Chen, {Shinn Horng} and Shiau, {Chuen Shiou} and Tsai, {Lin Ren} and Yun Chen",
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Poly(9,9-dihexylfluorene) derivatives containing electron-transporting aromatic triazole segments : Synthesis, optical and electrochemical properties. / Chen, Shinn Horng; Shiau, Chuen Shiou; Tsai, Lin Ren; Chen, Yun.

In: polymer, Vol. 47, No. 26, 08.12.2006, p. 8436-8443.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Poly(9,9-dihexylfluorene) derivatives containing electron-transporting aromatic triazole segments

T2 - Synthesis, optical and electrochemical properties

AU - Chen, Shinn Horng

AU - Shiau, Chuen Shiou

AU - Tsai, Lin Ren

AU - Chen, Yun

PY - 2006/12/8

Y1 - 2006/12/8

N2 - We prepared three new poly(9,9-dihexylfluorene) derivatives (P1-P3) containing kinked aromatic triazole (triphenyl-1,2,4-triazole derivative) via Suzuki coupling polymerization. These copolymers were soluble in common organic solvents and showed high decomposition temperatures (Td = 416-454 °C). The optical and electrochemical properties of P1-P3 were compared with poly(9,9-dihexylfluorene) (PFO) and P4 and P5 in which the linkages of the aromatic triazole were different. After introducing the triazole units, absorption spectra showed blue shift (388 nm → 372 nm) due to reduced conjugation, but PL spectra remained almost unchanged (417-418 nm). The linkages of triazole with fluorene segments in P1-P5 were different: (1) fluorene segments linked with triazole through a kinked angle (P1 and P2), (2) triazole as a branch unit (P3) and as terminal groups (P4), (3) fluorene segments linked with triazole in a linear way (P5). As estimated from semi-empirical MNDO calculation, two twisted conformations (ca. 90° each) exist between triazole core and fluorene groups. These kinked conformation and twisted structure increased the PL efficiency (ΦPL = 0.60-0.73, ΦPL = 0.58 for PFO) and partially inhibited annealing-induced excimer formation. From cyclic voltammetric results, P1-P3 exhibited better electron affinity (LUMO: -2.75 to -2.82 eV) than PFO (LUMO: -2.52 eV).

AB - We prepared three new poly(9,9-dihexylfluorene) derivatives (P1-P3) containing kinked aromatic triazole (triphenyl-1,2,4-triazole derivative) via Suzuki coupling polymerization. These copolymers were soluble in common organic solvents and showed high decomposition temperatures (Td = 416-454 °C). The optical and electrochemical properties of P1-P3 were compared with poly(9,9-dihexylfluorene) (PFO) and P4 and P5 in which the linkages of the aromatic triazole were different. After introducing the triazole units, absorption spectra showed blue shift (388 nm → 372 nm) due to reduced conjugation, but PL spectra remained almost unchanged (417-418 nm). The linkages of triazole with fluorene segments in P1-P5 were different: (1) fluorene segments linked with triazole through a kinked angle (P1 and P2), (2) triazole as a branch unit (P3) and as terminal groups (P4), (3) fluorene segments linked with triazole in a linear way (P5). As estimated from semi-empirical MNDO calculation, two twisted conformations (ca. 90° each) exist between triazole core and fluorene groups. These kinked conformation and twisted structure increased the PL efficiency (ΦPL = 0.60-0.73, ΦPL = 0.58 for PFO) and partially inhibited annealing-induced excimer formation. From cyclic voltammetric results, P1-P3 exhibited better electron affinity (LUMO: -2.75 to -2.82 eV) than PFO (LUMO: -2.52 eV).

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JF - Polymer

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