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Chemical Structure| 3005-27-4 Chemical Structure| 3005-27-4

Structure of 3005-27-4

Chemical Structure| 3005-27-4

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Product Citations

Product Citations

Sarah M. West ; Duyen K. Tran ; Jiajie Guo ; Shinya E. Chen ; David S. Ginger ; Samson A. Jenekhe

Abstract: In this work, we show how N-alkyl substitution affects the chain conformation, electronic structure, and optical and charge transport properties of π-conjugated ladder poly(pyrrolobenzothiazines)s (LPBTs). We found that the π-conjugated backbones of the LPBTs have a donor–acceptor motif, which enabled a small bandgap of 1.5 eV that is unchanged by N-alkyl substitution. We found that partial protonation of the LPBTs in acid solutions resulted in increased backbone flexibility evidenced by thermochromism in solution and planar/nonplanar chain conformational variation with degree of protonation that we saw in density functional theory (DFT) calculations. The average field-effect hole mobility increased from 1.3 × 10[–3] cm2/(V s) in LPBT-Me to 3.1 × 10[–3] cm2/(V s) in LPBT, which can be explained by the increased crystallinity and decreased lattice disorder in LPBT. The results of our investigations of the solution and solid-state properties of the two ladder poly(pyrrolobenzothiazine)s provide new insights into the structure–property relationships of π-conjugated ladder polymers.

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Product Details of [ 3005-27-4 ]

CAS No. :3005-27-4
Formula : C5H3Br2NO2
M.W : 268.89
SMILES Code : O=C(N1C)C(Br)=C(Br)C1=O
MDL No. :MFCD00102284
InChI Key :CKITYUQKOJMMOI-UHFFFAOYSA-N
Pubchem ID :18155

Safety of [ 3005-27-4 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302
Precautionary Statements:P264-P270-P301+P312-P501

Application In Synthesis of [ 3005-27-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 3005-27-4 ]

[ 3005-27-4 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 3005-27-4 ]
  • [ 7553-56-2 ]
  • [ 119139-23-0 ]
YieldReaction ConditionsOperation in experiment
65% Tetrahydrofuran (80mL), magnesium turnings (80.25 g, 0.33 moles) and iodine (0.5 g) were charged and stirred in a reaction flask equipped with mechanical stirrer, thermometer pocket, heating mantle, condenser, 500 mL addition funnel and nitrogen inlet. Slowly, ethyl bromide solution (30 mL, 0.40 moles) was added over one hour, maintaining the temperature below 40 C. the reaction mixture was further stirred at the mass temperature of 30-40 C, for another 30 minutes. Substituted indole (38.8 g, 0.333 moles) dissolved in toluene (81 mL) was charged to the addition funnel and was added dropwise over next one hour at temperature of 30- 40 C. A solution of dichloro-N-methylmaleimide (20.05 g, 0.1114 moles) in toluene (150 mL) was prepared and added slowly, during which time a dark heterogenous mixture resulted. The mixture was heated to reflux (temperature = 110 C) for one hour and monitored by TLC till the completion of the reaction (mobile phase: Chloroform : ethyl acetate = 6 : 1). The reaction mixture was cooled to 20-30 C. 20 % aqueous solution of citric acid (200 mL) slowly, at temperature below 5 C, in one hour. The slurry was further stirred at 0 C for 30 minutes. The red colored solid separates out. The product was isolated by filtration, rinsed with water and toluene, then dried in air. 28. 7 g (69.5 %) of product was obtained, melting range: 280 C (DSC), H. P. L. C. purity = 98.7 %. If desired, the above product can be further recrystallised from acetone to obtain the PHARMACEUTICALLY ACCEPTABLE purity of more than 99. 5 % (yield = 65 % overall yield).
 

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Technical Information

• Acyl Group Substitution • Alkyl Halide Occurrence • Baeyer-Villiger Oxidation • Barbier Coupling Reaction • Baylis-Hillman Reaction • Bucherer-Bergs Reaction • Chan-Lam Coupling Reaction • Clemmensen Reduction • Complex Metal Hydride Reductions • Corey-Bakshi-Shibata (CBS) Reduction • Corey-Chaykovsky Reaction • Fischer Indole Synthesis • General Reactivity • Grignard Reaction • Henry Nitroaldol Reaction • Hiyama Cross-Coupling Reaction • Horner-Wadsworth-Emmons Reaction • Hydride Reductions • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Lawesson's Reagent • Leuckart-Wallach Reaction • McMurry Coupling • Meerwein-Ponndorf-Verley Reduction • Passerini Reaction • Paternò-Büchi Reaction • Petasis Reaction • Peterson Olefination • Pictet-Spengler Tetrahydroisoquinoline Synthesis • Preparation of Aldehydes and Ketones • Preparation of Amines • Prins Reaction • Reactions of Aldehydes and Ketones • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Reactions of Dihalides • Reformatsky Reaction • Robinson Annulation • Schlosser Modification of the Wittig Reaction • Schmidt Reaction • Specialized Acylation Reagents-Carbodiimides and Related Reagents • Specialized Acylation Reagents-Ketenes • Stille Coupling • Stobbe Condensation • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling • Tebbe Olefination • Ugi Reaction • Wittig Reaction • Wolff-Kishner Reduction

Categories

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[ 3005-27-4 ]

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Related Parent Nucleus of
[ 3005-27-4 ]

Pyrrolines

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