Synthesis of Alkylated Aminofluorenes by Palladium-Catalyzed Substitution at Halofluorenes

Saroja, G.; Zhang, Pingzhu; Érnsting, N. P.; Liebscher, J.

doi:10.1021/jo035204n

Cited by 40 publications

(26 citation statements)

References 17 publications

(17 reference statements)

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“…de-ANF was purchased from Sigma-Aldrich (98%) and purified by chromatography on silica to yield the analytically pure material, and dm-ANF molecules were synthesized as described in literature. 35 Purification of dm-ANF was difficult, but achieved by repeated chromatography on silica, to yield the analytically pure material. NMR spectra of the pure compounds are presented in the ESI † ( Fig.…”

Section: Methodsmentioning

confidence: 99%

Solvent-dependent dual fluorescence of the push–pull system 2-diethylamino-7-nitrofluorene

Larsen

Stephansen

Alarousu

et al. 2018

Phys. Chem. Chem. Phys.

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The solvent-dependent excited state behavior of the molecular push-pull system 2-diethylamino-7-nitrofluorene has been explored using femtosecond transient absorption spectroscopy in combination with density functional theory calculations. Several excited state minima have been identified computationally, all possessing significant intramolecular charge transfer character. The experimentally observed dual fluorescence is suggested to arise from a planar excited state minimum and another minimum reached by twisting of the aryl-nitrogen bond of the amino group. The majority of the excited state population, however, undergo non-radiative transitions and potential excited state deactivation pathways are assessed in the computational investigation. A third excited state conformer, characterized by twisting around the aryl-nitrogen bond of the nitro group, is reasoned to be responsible for the majority of the non-radiative decays and a crossing between the excited state and ground state is localized. Additionally, ultrafast intersystem crossing is observed in the apolar solvent cyclohexane and rationalized to occur via an El-Sayed assisted transition from one of the identified excited state minima. The solvent thus determines more than just the fluorescence lifetime and shapes the potential energy landscape, thereby dictating the available excited state pathways.

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Section: Methodsmentioning

confidence: 99%

Solvent-dependent dual fluorescence of the push–pull system 2-diethylamino-7-nitrofluorene

Larsen

Stephansen

Alarousu

et al. 2018

Phys. Chem. Chem. Phys.

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“…[12] However, no trinuclear complex has been observed for CPP synthesis.Polyfluorenes,w hich contain rigid biphenyl unit, have emerged as an attractive class of conjugatedp olymers for applications to organic electronics due to excellent fluorescent and electroluminescence ability and high charge-carrier mobility of fluorene unit. [13] Therefore, synthesis of cyclic oligomers of fluorenederivativesw ould be of great interest.During the platinum-mediated synthesiso ft he cyclic fluorene derivatives, we found that the assembly of 2,7-bis(trimethylstannyl)-9,9-dimethyl-2,7-fluorene (1) [14] with [PtCl 2 (cod)] (cod = 1,5-cyclooctadiene) mainly afforded at riangle-shaped complex with ap latinum at each vertex. Reductivee limination of platinum from the trianglec omplex gave [3]cyclo-9,9-dimethyl-2,7-fluorene( [3]CFR).…”

mentioning

confidence: 99%

Ligand‐Controlled Synthesis of [3]‐ and [4]Cyclo‐9,9‐dimethyl‐2,7‐fluorenes through Triangle‐ and Square‐Shaped Platinum Intermediates

Kayahara

Kojima

et al. 2015

Chemistry A European J

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The syntheses of [3]- and [4]cyclo-9,9-dimethyl-2,7-fluorenes ([3] and [4]CFRs), cyclic trimer, and tetramers of 9,9-dimethyl-2,7-fluorene (FR), respectively, were achieved by the platinum-mediated assembly of FR units and subsequent reductive elimination of platinum. A triangle-shaped tris-platinum complex and a square-shaped tetra-platinum complex were obtained by changing the platinum ligand. The structure of the triangle complex was unambiguously determined by X-ray crystallographic analysis. Reductive elimination of each complex gave [3] and [4]CFRs. Two rotamers of [3]CFR were sufficiently stable at room temperature and were separated by chromatography. The physical properties of the CFRs were also investigated theoretically and experimentally.

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“…with an 80% yield [76]. The nitro groups of both 30 and 31 were efficiently reduced to amino functionality per our recent report on commercially available Fe 3 O 4 nanoparticles as a heterogeneous catalyst for nitro group reduction in combination with hydrazine monohydrate [77].…”

Section: Chemistrymentioning

confidence: 87%

Novel benzidine and diaminofluorene prolinamide derivatives as potent hepatitis C virus NS5A inhibitors

Bae

Kim

You

et al. 2015

European Journal of Medicinal Chemistry

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Synthesis of Alkylated Aminofluorenes by Palladium-Catalyzed Substitution at Halofluorenes

Cited by 40 publications

References 17 publications

Solvent-dependent dual fluorescence of the push–pull system 2-diethylamino-7-nitrofluorene

Solvent-dependent dual fluorescence of the push–pull system 2-diethylamino-7-nitrofluorene

Ligand‐Controlled Synthesis of [3]‐ and [4]Cyclo‐9,9‐dimethyl‐2,7‐fluorenes through Triangle‐ and Square‐Shaped Platinum Intermediates

Novel benzidine and diaminofluorene prolinamide derivatives as potent hepatitis C virus NS5A inhibitors

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