Cyclopenta-fused polyaromatic hydrocarbons: synthesis and characterisation of a stable, carbon-centred helical radical

Herzog, Stefan; Hinz, Alexander; Breher, Frank; Podlech, Joachim

doi:10.1039/d2ob00172a

Cited by 16 publications

(24 citation statements)

References 85 publications

(51 reference statements)

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“…This could be due to several reasons, namely, the fairly low availability of functionalized PAH synthons and their low solubility. 6,7 Pararosaniline hydrochloride, commonly known as basic red 9 or BR9, belongs to the triarylmethane organic dye family and is one of the four basic fuchsine dyes, where in addition to the latter, we note rosaniline, new fuchsine, and magenta II. 15 BR9 is employed as a coloring agent for myriad products, such as, paper, leather, textiles, glass, waxes, and cosmetics besides its use in the manufacture of inks and paints.…”

Section: Introductionmentioning

confidence: 99%

High Uptake of the Carcinogenic Pararosaniline Hydrochloride Dye from Water Using Carbazole-Containing Conjugated Copolymers Synthesized from a One-Pot Cyclopentannulation Reaction

Shetty,

Baig,

Bargakshatriya

et al. 2023

ACS Appl. Mater. Interfaces

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Three conjugated copolymers CAP1−3 were synthesized in one-step via a typical [3+2] cyclopentannulation reaction using a specially designed diethynyl carbazole synthon with various dibrominated polycondensed aromatic hydrocarbons (PAHs). The desired copolymers CAP1−3 were obtained in excellent yields, and their structures were confirmed by 1 H-and 13 C-nuclear magnetic spectroscopy (NMR), whereas gel permeation chromatography revealed weight-average molar masses (M w ) up to 19.9 kDa with a polydispersity index (PDI) in the range of 2.2−2.6. Interestingly, CAP1−3 exhibits an outstanding capacity to adsorb the carcinogenic pararosaniline hydrochloride dye (Basic Red 9, BR9) from aqueous solutions. Isothermal adsorption studies were carried out following the linear models of Langmuir and Freundlich, divulging an adsorption capacity maximum (q m ) toward BR9 of 483.09 mg g −1 . Investigation of the dye uptake mechanism on CAP1−3 revealed a pseudo-second-order kinetic model for the target copolymer that showed the highest uptake capacity. Recyclability tests disclosed an excellent adsorption efficiency of BR 9 reaching 93% after six cycles.

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Section: Introductionmentioning

confidence: 99%

High Uptake of the Carcinogenic Pararosaniline Hydrochloride Dye from Water Using Carbazole-Containing Conjugated Copolymers Synthesized from a One-Pot Cyclopentannulation Reaction

Shetty,

Baig,

Bargakshatriya

et al. 2023

ACS Appl. Mater. Interfaces

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“…This compound avoids planarity; it is helically chiral and consequently meets the definition for helicenes. 4…”

Section: Introductionmentioning

confidence: 99%

“…This compound avoids planarity; it is helically chiral and consequently meets the definition for helicenes. 4 Figure 1 [5]Helicene (1), diaza [5]helicenes 2 and 3, and carbazole-derived [5]helicene 4…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Diaza[5]helicenes by ortho,ortho′-Fusion of ortho-Terphenyls

et al. 2022

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Double ortho-fusion in suitably substituted ortho-terphenyls are used for the synthesis of diaza[5]helicenes. Bis(carboxamido)-substituted ortho-terphenyls can be condensed to 5,9- and 6,9-diaza[5]helicenes, where substituents at the 5,9- and 6,9-positions, respectively, are introduced with the carboxamido groups. While a twofold coupling sequence with intermediate protection of one amino group has to be used for 5,9-diaza[5]helicenes, a more concise sequence avoiding the protection leads to 6,9-diaza[5]helicenes. The simple heating of ortho,ortho’-diazido-terphenyls furnishes 5,8-dihydroindolo[2,3-c]carbazoles, i.e., [5]helicenes with alternating benzene and pyrrol rings.

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“…A helical fragment of 1 with seven alternatingly fused 6–5–6–5–6–5–6 rings in a doublet ground state was reported . It was Wu’s group that synthesized a stable closed-shell s -indacenodifluorene ( s -IDF) 2 (Figure e), which was based on Tobe’s [1,2- b :5,6- b ′] s -IDF scaffold (Figure b) …”

mentioning

confidence: 99%

“…6 A helical fragment of 1 with seven alternatingly fused 6−5− 6−5−6−5−6 rings in a doublet ground state was reported. 7 It was Wu's group that synthesized a stable closed-shell sindacenodifluorene (s-IDF) 2 (Figure 1e), 8 which was based on Tobe's [1,2-b:5,6-b′]s-IDF scaffold (Figure 1b). 5 s-IDF 2 is a fragment of the fully conjugated ladder oligo(ININ) [or OININ] which was recently investigated by on-surface synthesis.…”

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confidence: 99%

Dominating Antiaromatic Character of as-Indacene Decides Overall Properties of a Formally Aromatic Dicyclopenta[c]fluorenothiophene

et al. 2023

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Dicyclopenta[c]fluorenothiophene 5 was synthesized as the isoelectronic polycyclic heteroarene analogue of an as-indacenodifluorene with a (4n + 2)π-electron perimeter. Single-crystal and 1 H NMR analyses indicated a quinoidal ground state for 5, which was supported by theoretical calculations while suggesting a degree of antiaromaticity of the as-indacene subunit greater than that for sindacenodifluorene 3. The dominant antiaromaticity for 5 was evidenced by the broad weakly intense absorption tail reaching the near-IR region, four-stage redox amphotericity, and small HOMO− LUMO energy gap.

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Cyclopenta-fused polyaromatic hydrocarbons: synthesis and characterisation of a stable, carbon-centred helical radical

Abstract: An air- and moisture-stable helical radical with seven six- and five-membered rings arranged alternately was synthesized by cyclizations in a suitably ortho,ortho’-substituted terphenyl and re-stablishing of its conjugation. Mesityl groups...

Cited by 16 publications

References 85 publications

High Uptake of the Carcinogenic Pararosaniline Hydrochloride Dye from Water Using Carbazole-Containing Conjugated Copolymers Synthesized from a One-Pot Cyclopentannulation Reaction

High Uptake of the Carcinogenic Pararosaniline Hydrochloride Dye from Water Using Carbazole-Containing Conjugated Copolymers Synthesized from a One-Pot Cyclopentannulation Reaction

Synthesis of Diaza[5]helicenes by ortho,ortho′-Fusion of ortho-Terphenyls

Dominating Antiaromatic Character of as-Indacene Decides Overall Properties of a Formally Aromatic Dicyclopenta[c]fluorenothiophene

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