Semi-perfluoroalkyl polyfluorene with varying fluorine content: synthesis and photophysical properties

McCluskey, Georgia E.; Watkins, Scott E.; Holmes, Andrew B.; Ober, Christopher K.; Lee, Jin‐Kyun; Wong, Wallace W. H.

doi:10.1039/c3py00124e

Cited by 8 publications

(3 citation statements)

References 21 publications

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“…The extent of the blue shift of ultraviolet absorption peaks in solution and film state increases with the increase of the content of fluorinated structural units in copolymers. It is believed that fluorine atoms on the side chain in the copolymers are highly electronegative, which makes the side chain and the conjugated main chain form strong interaction, resulting in the distortion of the conjugated main chain and UV–vis absorption spectra blue shift 34 …”

Section: Resultsmentioning

confidence: 99%

Synthesis and performances of 9,9‐bis(perfluorohexylethyl propionate) fluorene copolymers

Wang

et al. 2021

J of Applied Polymer Sci

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2,7‐dibromo‐9,9‐bis(perfluorohexylethyl propionate) fluorene was synthesized by Michael addition reaction using 2,7‐dibromofluorene and perfluorohexyl ethyl acrylate as the reactants. 9,9‐Bis(perfluorohexylethyl propionate) fluorene copolymers were then synthesized by Suzuki coupling reaction with 2,7‐bis(4,4,5,5‐tetramethyl‐1,3,2‐dioxaborane‐diyl)‐9,9 ‐dioctyl fluorene, 2,7‐dibromo‐9,9‐dioctyl fluorene and 2,7‐dibromo‐9,9‐bis(perfluorohexylethyl propionate) fluorene as the monomers. The fluorinated fluorene copolymers were characterized and investigated via Fourier infrared spectroscopy (FTIR), hydrogen nuclear magnetic resonance spectroscopy (1HNMR), ultraviolet absorption spectroscopy (UV–vis), cyclic voltammetry (CV) and photoluminance spectroscopy (PL). Because of the long fluorine‐containing alkyl side chain, the ultraviolet absorption peak of 9,9‐bis(perfluorohexylethyl propionate) fluorene is blue‐shifted compared with poly(9,9‐dioctylfluorene)(PF8). The LUMO energy level increases and the energy band gap of copolymers widens. Due to the self‐assembly of the long fluoroalkyl side chain, the photoluminance spectra of 9,9‐bis(perfluorohexylethyl propionate) fluorene copolymers exhibit a new excimer emission peak at 550 nm. The photoluminance stabilities of the copolymers under irradiation and humid conditions are significantly improved due to protective effect from the long fluoroalkyl side chain. After being irradiated under 500 W iodine tungsten lamp or kept under 70% relative humid conditions, the 9,9‐bis(perfluorohexylethyl propionate) fluorene copolymers showed much better photoluminance stability than that of poly(9,9‐dioctylfluorene) (PF8). These show that introducing long fluoroalkyl side chain into conjugated polymer main chain is a promising strategy to improve environmental stability of devices based on organic conjugated polymers.

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Section: Resultsmentioning

confidence: 99%

Synthesis and performances of 9,9‐bis(perfluorohexylethyl propionate) fluorene copolymers

Wang

et al. 2021

J of Applied Polymer Sci

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“…Other application are microelectronics where they are mainly used as low dielectric constants materials due to low polarizability of CF bond . Their unique self‐assembly and orthogonal (hydrophobic and lipophobic) properties promote their use in organic semiconductors …”

Section: Introductionmentioning

confidence: 99%

Nanoindentation of Films of Perfluorotridecyl, Perfluorodecyl, and Perfluoroheptyl End‐Functionalized Polystyrene at the Micron Scale

Yurdacan

Franke

Hogen‐Esch

2016

Macro Chemistry & Physics

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Polystyrenes (PS) end-functionalized with perfl uorotridecyl (PFTD), perfl uorodecyl (PFD), and perfl uoroheptyl (PFH) groups are synthesized using the corresponding perfl uoroalkyl initiators by atom transfer radical polymerization. Polymer thin fi lms deposited on silicon wafers are studied by dynamic nanoindentation (NI). NI measurements of the 15k PFTD-PS sample showed increases of about 80 and 300% in the storage and loss moduli, respectively, compared to the 15k PS homopolymer. Measurements made on different regions of the PFTD-functionalized PS show a fi vefold greater standard deviation compared to the 15k PS homopolymer. The effects for the PFD and PFH groups are smaller in all respects consistent with expectations.

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“…The exact origin of this low-energy emission band remains unclear. 14 Nevertheless various efforts have been made to address this disadvantage, including using either dendrimers or bulky substituents in the 9-position of the uorene moiety, 15,16 copolymerization techniques, 17,18 purication of the uorene monomers before polymerization, 19 or blends of PFs with some nonconjugated polymers such as polystyrene (PS) or poly(vinyldiphenylquinoline), 20 while the undesirable emission band was not eliminated. 21 In recent studies, coil-like blocks nonconjugated and hole/ electron transporting molecules were incorporated into poly-uorene backbones to suppress the aforementioned low-energy emission.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of polyfluorene-based photoelectric materials: the effect of coil segment on the spectral stability

Wang

Zhou

et al. 2014

RSC Adv.

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Semi-perfluoroalkyl polyfluorene with varying fluorine content: synthesis and photophysical properties

Cited by 8 publications

References 21 publications

Synthesis and performances of 9,9‐bis(perfluorohexylethyl propionate) fluorene copolymers

Synthesis and performances of 9,9‐bis(perfluorohexylethyl propionate) fluorene copolymers

Nanoindentation of Films of Perfluorotridecyl, Perfluorodecyl, and Perfluoroheptyl End‐Functionalized Polystyrene at the Micron Scale

Synthesis and characterization of polyfluorene-based photoelectric materials: the effect of coil segment on the spectral stability

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