Synthèse d'analogues furanniques du benzo[<i>a</i>]pyrène

Demerseman, P.; Einhorn, Jacques; Royer, R.; Gourvest, Jean-François

doi:10.1002/jhet.5570220110

Cited by 30 publications

(11 citation statements)

References 9 publications

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“…It is obtained in eight steps starting from 1‐methoxypyrene. The first step starts with an ortho ‐lithiation followed by condensation on CO 2 and then methylation of the carboxylate with methyl iodide to provide compound 2 in 64 % yield [32] . Then, the methoxy function is turned out into a bromo atom in four steps starting by demethylation ( 3 ), followed by a triflation ( 4 ), borylation ( 5 ) via a cross‐coupling reaction and then the conversion of pinacolboronate into a bromo atom using CuBr 2 to provide compound 6 [33] .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

et al. 2021

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We report the synthesis and optoelectronic properties of TIPS‐peri‐pentacenopentacene (TIPS‐PPP), a vertical extension of TIPS‐pentacene (TIPS‐PEN) and a low‐band‐gap material with remarkable stability. We found the synthetic conditions to avoid the competition between 1,2‐ and 1,4‐addition of lithium acetylide on the large aromatic dione. The high stability of TIPS‐PPP is due to the peri‐fusion which increases the aromaticity by generating two localized aromatic sextets that are flanked with 2 diene fragments, similar to two fused‐anthracenes. Like TIPS‐PEN, TIPS‐PPP shows the archetypal 2D brickwall motif in crystals with a larger transfer integral and smaller reorganization energy. The high mobility of up to 1 cm2 V−1 s−1 was obtained in an organic field‐effect transistor fabricated by a wet process. Also, TIPS‐PPP was used as a near‐infrared (NIR) emitter for NIR organic‐light‐emitting‐diode devices resulting in a high external quantum efficiency at 800 nm.

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Section: Resultsmentioning

confidence: 99%

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

et al. 2021

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“…It is obtained in eight steps starting from 1-methoxypyrene.T he first step starts with an ortho-lithiation followed by condensation on CO 2 and then methylation of the carboxylate with methyl iodide to provide compound 2 in 64 %yield. [32] Then, the methoxy function is turned out into abromo atom in four steps starting by demethylation (3), followed by at riflation (4), borylation (5)v ia across-coupling reaction and then the conversion of pinacolboronate into ab romo atom using CuBr 2 to provide compound 6. [33] Theg lobal yield for this sequence is 65 %.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

et al. 2021

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We report the synthesis and optoelectronic properties of TIPS-peri-pentacenopentacene (TIPS-PPP), av ertical extension of TIPS-pentacene (TIPS-PEN)a nd al ow-band-gap material with remarkable stability.W ef ound the synthetic conditions to avoid the competition between 1,2-and 1,4addition of lithium acetylide on the large aromatic dione.The high stability of TIPS-PPP is due to the peri-fusion which increases the aromaticity by generating two localized aromatic sextets that are flanked with 2d iene fragments,s imilar to two fused-anthracenes.L ike TIPS-PEN, TIPS-PPP shows the archetypal 2D brickwall motif in crystals with alarger transfer integral and smaller reorganization energy.T he high mobility of up to 1cm 2 V À1 s À1 was obtained in an organic field-effect transistor fabricated by aw et process.A lso, TIPS-PPP was used as an ear-infrared (NIR) emitter for NIR organic-lightemitting-diode devices resulting in ah igh external quantum efficiency at 800 nm.

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“…FP1, FP2 and FP3 were recently synthesized (6,7). NADPH (6-Nicotinamide Adenine Dinucleotide Phosphate) was purchased from Sigma Chemical Co.…”

Section: Materials and Methods Chemicalsmentioning

confidence: 99%

“…Three isomers of pyrenofuran were synthesized as analogues of B(a)P and B(e)P. A five membered heterocycle containing an oxygen atom replaces in each case the external benzene ring of B(a)P or B(e)P. Two B(a)P-like molecules have been synthesized with a different location of the oxygen atom : the pyreno[l,2-blfuran (FP1) and the pyreno [2,1-b]furan (FP2) (6). Because of the B(e)P symmetry, only one B(e)P like molecule can be synthesized : the pyreno [4,5-b]furan (FP3) (7) (see figure 1 for the structures).…”

Section: Introductionmentioning

confidence: 99%

Reactivity with DNA of three pyrenofuran analogues of benzo(a)pyrene and benzo(e)pyrene

Jollès¹,

Demerseman

Chalvet³

et al. 1987

Nucl Acids Res

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Three pyrenofurans, the pyreno[1,2-b]furan (FP1), the pyreno[2,1-b] furan (FP2) and the pyreno[4,5-b]furan (FP3) have been synthesized as analogues of the mutagenic and carcinogenic benzo(a)pyrene (FP1 and FP2) and of its non-carcinogenic isomer benzo(e)pyrene (FP3). For each of the pyrenofurans, the reactivity with DNA has been tested in presence of liver microsomes of rats induced with 3-methylcholanthrene. Fluorescence spectroscopy showed that only FP2 and FP3 which possess a "bay region" react with DNA. In both cases, metabolites bound to DNA have a fluorescence emission comparable to that of the "bay region" dihydrodiols obtained after the "in vitro" metabolism of initial molecules. FP2 is shown to react similarly to benzo(a)pyrene whereas the reactivity of FP3 is different from that of benzo(e)pyrene, in spite of their structural similarities. This is probably due to reasons of three-dimensional space configuration. The peculiar reactivity of FP3 is predicted by calculations of the bond order values.

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Synthèse d'analogues furanniques du benzo[a]pyrène

Abstract: On décrit les synthèses à partir du bromo‐1 pyrène, des deux analogues furanniques du benzo[a]pyrène, les pyréno[1,2‐b]furanne et pyréno[2,1‐b]furanne, ainsi que de leurs dérivés nitrés sur l'hétérocycle.

Cited by 30 publications

References 9 publications

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Synthesis, Aromaticity, and Application of peri‐Pentacenopentacene: Localized Representation of Benzenoid Aromatic Compounds

Reactivity with DNA of three pyrenofuran analogues of benzo(a)pyrene and benzo(e)pyrene

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