A Convenient Synthesis of of Their Spectroscopic And

Pham, Chiem Van; Burkhardt, A.; Shabanas, R.; Cunningham, David; Mark, Harry B.; Zimmer, H.

doi:10.1080/10426508908045037

Cited by 26 publications

(33 citation statements)

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“…Sublimation (0.2 mmHg, 80 "C) gave a white solid (10.02 g, 75 mmol, 2.6 and 1. 4 Hz,lH,6.53 (dd, J = 3.5 and 1. 3 Hz,lH,6.23 (C=O), 138.8 (C-ipso (phenyl)), 133.6 (C-para), 132.7 (C-2), 130.3 (C-5), 128.7-128.0 (C-ortho, C-metal, 123.9 (C-3), 110.5…”

Section: N-(tert-butoxycarbonyl)-2s-dibromopyrrole (2)lzd N-mentioning

confidence: 99%

“…IH-NMR (CDC13): 6 9.96 (s, lH, H-ald. ), 7.93 (d, J = 8.2 Hz, 2H, H-ortho), 7.65 (m, 2H, H-para, H-51, 7.55 (t, J = 7.8 Hz, 2H, H-meta), 7.17 (dd, J = 3.8 and 1.7 Hz,lH,6.43 (t, J = (C-ipso (phenyl)), 134.5 (C-para), 133.5 (C-21, 129.5 (C-ortho and (2-51, 127.4 (C-metal, 124.9 (C-31, 112.5 ((2-4). (N-(phenylsulfonyl) -2-pyrryl) -1,4…”

Section: N~-bi~-tert-(butoxycarbony1)-2~-bipyrrole (5)mentioning

confidence: 99%

“…A slightly brown solid was obtained (3.34 g, 6.7 mmol, 45%). 'H-NMR (CDC13): 6 7.96 (d, J = 7.4 Hz, 4H, H-ortho), 7.80 (dd, J = 3.2 and 1.7 Hz, 2H, H-5), 7.58 (t, J = 7.4 Hz, 2H, H-para), 7.50 (t, J = 7.3 Hz, 4H, H-metal, 7.12 (dd, J = 3.8 and 1.7 Hz, 2H, H-3), 6.35 (t, J = and extracted with Et20. The organic fractions were dried (MgS04) and the solvent was evaporated resulting in dark oils which were filtered over A1203, using CHzClz as eluent, before HPLC analysis.…”

Section: -Butanedione @)I9mentioning

confidence: 99%

“…N,"-Bis(tert-butoxycarbonyl-5,5'-dibromo-2,2-bipp role (6). N,N'-Bis(tert-butoxycarbonyl)-2,2'-bipyrrole (5,85.0 mg, 0.256 mmol) was solved in THF (4.5 mL) and cooled to -70 "C. NBS (91.0 mg, 0.511 mmol) was added and the mixture was stirred for 30 min at -70 "C. Then it was warmed to 3 "C at which temperature it was kept for 3 h. NazS03 (a few mg) was added, and the solvent was evaporated.…”

Section: N~-bi~-tert-(butoxycarbony1)-2~-bipyrrole (5)mentioning

confidence: 99%

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Well-Defined Oligo(pyrrole-2,5-diyl)s by the Ullmann Reaction

Groenendaal¹,

Peerlings²,

Dongen³

et al. 1995

Macromolecules

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The Ullmann coupling reaction has been used to polymerize N-t-BOC-2,5-dibromopyrrole into well-defined oligo(pyrrole-2,5-diyl)s. After optimization of the reaction conditions, i.e. using 1 wt equiv of Cu-bronze in DMF at 100 "C for 1 h, oligomers up to 25 repeating pyrrole units are obtained.Starting from 5,5'-and 5,5"-dibrominated N-t-BOC protected bi-and terpyrrole as monomers, the polymerization is slower and a lower degree of polymerization is observed, yielding oligomers with an even lower molecular weight than those resulting from N-t-BOC-2,5-dibromopyrrole. The first 20 oligomers of poly(N-t-BOC-pyrrole) have been isolated by preparative HPLC. Characterization of the individual oligomers shows that they all are hydrogen terminated and possess a perfect 2,5-linkage: oligo(pyrro1e-2,5-diyl)s. The isolated oligomers have been used to study the optical and electrical properties of the oligomers as a function of chain length.

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Section: N-(tert-butoxycarbonyl)-2s-dibromopyrrole (2)lzd N-mentioning

confidence: 99%

Section: N~-bi~-tert-(butoxycarbony1)-2~-bipyrrole (5)mentioning

confidence: 99%

Section: -Butanedione @)I9mentioning

confidence: 99%

Section: N~-bi~-tert-(butoxycarbony1)-2~-bipyrrole (5)mentioning

confidence: 99%

See 2 more Smart Citations

Well-Defined Oligo(pyrrole-2,5-diyl)s by the Ullmann Reaction

Groenendaal¹,

Peerlings²,

Dongen³

et al. 1995

Macromolecules

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“…In unsubstituted oligothiophenes, the degree of oligomerization can be easily followed from the red shift of the electron transfer band, located at 243 nm for thiophene, 302 nm for bithiophene and shifting up to 432 nm in the oligomer 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 containing five thiophene units. [13] The presence of the large delocalized p system of helicene in the 3-([7]helicen-9-yl)thiophene monomer, oligomers and polymers results in the spectra containing broad and overlapping features, rendering quantitative estimation of the mean degree of conjugation of polymers impossible. Qualitatively, red shifts in long wavelength absorption bands indicate an increasingly higher level of conjugation in the order 3-([7]helicen-9-yl)-thiophene monomer < non-conductive oligomer < conductive oligomer < nonconductive polymer < conductive polymer.…”

mentioning

confidence: 99%

Potential‐Driven On/Off Switch Strategy for the Electrosynthesis of [7]Helicene‐Derived Polymers

et al. 2017

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New materials bearing thiophene and helicene moieties were prepared by using a potential‐driven on/off switch strategy on the surface of glassy carbon and indium tin oxide substrates. Specifically, a 3‐([7]helicen‐9‐yl)‐thiophene hybrid monomer was electrooxidized in acetonitrile by using cyclic voltammetry with anodic potential limits of +1.5 or +2.5 V, resulting in a conductive and non‐conductive polymer, respectively. The electrochemical findings were supplemented by microscopy investigations, UV/Vis, fluorescence and vibrational spectroscopies, and 1H NMR spectroscopy as well as ellipsometry measurements and computational chemistry. The electrodeposited polymers could be used for the further development of materials applicable in organic electronics, optoelectronics, and sensing technologies.

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Thiophene–Benzothiadiazole Co‐Oligomers: Synthesis, Optoelectronic Properties, Electrical Characterization, and Thin‐Film Patterning

Melucci

Favaretto

Zanelli

et al. 2010

Adv Funct Materials

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Newly synthesized thiophene (T) and benzothiadiazole (B) co‐oligomers of different size, alternation motifs, and alkyl substitution types are reported. Combined spectroscopic data, electrochemical analysis, and theoretical calculations show that the insertion of a single electron‐deficient B unit into the aromatic backbone strongly affects the LUMO energy level. The insertion of additional B units has only a minor effect on the electronic properties. Cast films of oligomers with two alternated B rings (B–T–B inner core) display crystalline order. Bottom‐contact FETs based on films cast on bare SiO2 show hole‐charge mobilities of 1 × 10−3–5 × 10−3 cm2 V−1s−1 and Ion/Ioff ratios of 105–106. Solution‐cast films of cyclohexyl‐substituted compounds are amorphous and do not show FET behavior. However, the lack of order observed in these films can be overcome by nanorubbing and unconventional wet lithography, which allow for fine control of structural order in thin deposits.

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A Convenient Synthesis of of Their Spectroscopic And

Cited by 26 publications

References 0 publications

Well-Defined Oligo(pyrrole-2,5-diyl)s by the Ullmann Reaction

Well-Defined Oligo(pyrrole-2,5-diyl)s by the Ullmann Reaction

Potential‐Driven On/Off Switch Strategy for the Electrosynthesis of [7]Helicene‐Derived Polymers

Thiophene–Benzothiadiazole Co‐Oligomers: Synthesis, Optoelectronic Properties, Electrical Characterization, and Thin‐Film Patterning

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