Covalent binding of redox active centres to preformed regioregular polythiophenes

Iraqi, Ahmed; Crayston, Joe A.; Walton, John C.

doi:10.1039/a703397d

Cited by 51 publications

(44 citation statements)

References 33 publications

(2 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Figure 1 shows the 1 H NMR spectra of 1 and 8. This 97% displacement is larger than the 87% reported by Iraqi et al 6 in displacement on the HTregioregular version of 1 with a carboxylate nucleophile and is similar to the report of Zhai, et al…”

Section: Bromine and Iodine Containing Polymerssupporting

confidence: 89%

“…The four resonances for 1/2 at δ 6.98, 7.01, 7.03 and 7.06/7.05 are assigned to HT-HT, HT-TT, HT-HH, TT-HH triad configurations, respectively. 14,15 It should be noted that the HT-HT peak at δ 6.98 compares quite favorably with the value of δ 6.98 reported by Iraqi, et al 6 and δ 6.95 reported recently by Zhai, et al for the HT-regioregular version of 1. 8 In addition, the peaks reported by Ng, et al agree with those we observed and, while in our hands the HT dyad is 81% of the polymer, they report that their polymer 1 has only 68-73% HT dyads.…”

Section: Bromine and Iodine Containing Polymerssupporting

confidence: 86%

“…4,5 About the same time as our initial preliminary report 4 Iraqi et al reported on the preparation of head-to-tail regioregular polymer 1. 6 The following year Ng et al reported on the synthesis of three poly [3-( -bromoalkyl)thiophene] polymers 7 using our reported methodology but failed to cite the prior publications. [4][5][6] Very recently a paper appeared reporting on head-to-tail regioregular polymer 1 and on several other polymers derived from 1 by post-polymerization reactions where the bromine acts as a leaving group.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis and study of poly(3-hexylthiophenes) and poly(3-dodecylthiophenes) containing halogen and sulfur substituents in the ω-position of the side chain

Pomerantz¹,

Liu²,

Zhang³

2003

Arkivoc

View full text Add to dashboard Cite

Poly [3-(6-bromohexyl)thiophene] (1) and poly [3-(12-bromododecyl)thiophene] (2) were synthesized by chemical polymerization of their respective monomers, 3 and 4, using FeCl 3 . NMR spectroscopy showed 81% of head-to-tail couplings and GPC showed M n = 51,500 and 91,100 with PDIs of 5.2 and 1.7 for 1 and 2, respectively. Conductivities of the I 2-and FeCl 3-doped 1 were 18 and 7.5 S cm -1 and for 2 were 32 and 46 S cm -1 , respectively. Poly[3-(6-iodohexyl)thiophene] (8) was prepared by S N2 displacement (>97%), using NaI, on 1. Poly[6-(3-thienyl)-1-hexyl S-thioacetate] (10a) and poly[12-(3-thienyl)-1-dodecyl S-thioacetate] (10b) were prepared from 1 by post-polymerization S N2 reactions. They were insoluble in organic solvents and had 13C CP-MAS NMR spectra consistent with the structures. Reaction of 1 with thiourea followed by basic hydrolysis gave poly[3-(6-mercaptohexyl)thiophene] (11). This thiol functionalized polymer was also insoluble in common organic solvents and it, too, had a 13 C CP-MAS NMR spectrum consistent with the structure. Polymers 10a and 11 showed pressed pellet conductivities of 4 x 10 -5 and 2.3 x 10 -2 S cm -1 when doped with FeCl 3 , respectively and 8 x 10 -5 and 0.44 S cm -1 when doped with I 2 , respectively. TGA of polymers 1, 8 and 11 showed thermal decomposition in two stages.

show abstract

Section: Bromine and Iodine Containing Polymerssupporting

confidence: 89%

Section: Bromine and Iodine Containing Polymerssupporting

confidence: 86%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Synthesis and study of poly(3-hexylthiophenes) and poly(3-dodecylthiophenes) containing halogen and sulfur substituents in the ω-position of the side chain

Pomerantz¹,

Liu²,

Zhang³

2003

Arkivoc

View full text Add to dashboard Cite

show abstract

“…The covalent binding of anthraquinone to regioregular poly[3-(6-bromohexyl)thiophene] has been reported. [12] Unlike other work on post-polymerization functionalization, derivatization in that case was performed on a polymer solution. Bäuerle et al have reported the postpolymerization functionalization of alkyl-substituted PTs, bearing terminal N-hydroxysuccinimide esters as easily replaceable leaving groups.…”

mentioning

confidence: 99%

Rapid and Efficient Post-Polymerization Functionalization of Poly(3,4-ethylenedioxythiophene) (PEDOT) Derivatives on an Electrode Surface

et al. 2001

View full text Add to dashboard Cite

First examples of post‐polymerization functionalization of poly(3,4‐ethylenedioxythiophene) (PEDOT) derivatives are reported using tetrathiafulvalene (TTF) as a redox sensitive probe. EDOT derivatives bearing ω‐iodo‐alkyl or ω‐iodo‐polyether chains attached at the ethylenedioxy bridge have been electropolymerized and the resulting polymers have been derivatized using a TTF bearing a thiolate anion liberated under mild conditions. Cyclic voltammetry confirms the rapidity and efficiency of the derivatization process. This facile post‐polymerization functionalization coupled with the unique properties of PEDOT should lead to interesting developments in the field of modified electrodes, which includes selective electrochemical sensors.

show abstract

“…The delocalized p bonds facilitated the electron movement and transfer, resulting in the enhancement of the electrical conductivity of CÀCNN, which was consistent with that in literature. [43,44] Therefore, the enhanced electrical conductivity of CÀCNN accelerated electron transfer, increased sulfur utilization, and contributed to the good rate performance.…”

mentioning

confidence: 99%

Polar Ultrathin Self‐Doping Carbon Nitride Nanosheets with Intrinsic Polysulfide Adsorption for High Performance Lithium‐Sulfur Batteries

Gong

Dong

et al. 2018

Batteries & Supercaps

View full text Add to dashboard Cite

Lithium-sulfur (LiÀS) batteries are promising for next-generation electrochemical energy storage due to their high energy density and low cost. Here, we introduce light-weight polar carbon selfdoping C 3 N 4 nanosheets (CÀCNN) as sulfur host for the fabrication of high performance LiÀS batteries. The role of carbon doping in boosting the electrical conductivity of CÀCNN is revealed by electrochemical impedance spectroscopy and electrical conductivity measurements. The strong chemical interactions between CÀCNN and polysulfides are investigated by adsorption and post-mortem X-ray photoelectron spectroscopy analysis. Benefiting from the high surface area, enhanced electrical conductivity and high content of active N species (56.7 at %) in CÀCNN, the strong chemical interactions between CÀCNN and polysulfides can be fully exploited to minimize the shuttle effect and achieve long cycle life of LiÀS batteries. As a result, the CÀCNN/S cathode delivers a high specific capacity of 1050 mAh g À1 , good rate capability and excellent cycling stability with a low capacity decay of 0.07 % per cycle at 1 C over 500 cycles, showing better performance than nitrogendoped graphene. A performance comparison with the literature also shows that CÀCNN is one of the most promising nitrogencontaining carbon materials for long cycle life LiÀS batteries.

show abstract

Covalent binding of redox active centres to preformed regioregular polythiophenes

Cited by 51 publications

References 33 publications

Synthesis and study of poly(3-hexylthiophenes) and poly(3-dodecylthiophenes) containing halogen and sulfur substituents in the ω-position of the side chain

Synthesis and study of poly(3-hexylthiophenes) and poly(3-dodecylthiophenes) containing halogen and sulfur substituents in the ω-position of the side chain

Rapid and Efficient Post-Polymerization Functionalization of Poly(3,4-ethylenedioxythiophene) (PEDOT) Derivatives on an Electrode Surface

Polar Ultrathin Self‐Doping Carbon Nitride Nanosheets with Intrinsic Polysulfide Adsorption for High Performance Lithium‐Sulfur Batteries

Contact Info

Product

Resources

About