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1 article(s) from Broløs, Line

Multi-redox indenofluorene chromophores incorporating dithiafulvene donor and ene/enediyne acceptor units

Christina Schøttler,
Kasper Lund-Rasmussen,
Line Broløs,
Philip Vinterberg,
Ema Bazikova,
Viktor B. R. Pedersen and
Mogens Brøndsted Nielsen

Beilstein J. Org. Chem. 2024, 20, 59–73, doi:10.3762/bjoc.20.8

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Graphical Abstract

Figure 1: Overview of structural motifs relevant for the work described herein.

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Figure 2: Dione/ketones 1, 4–6 and 1,3-dithiole-2-thione compounds 2, 3, 7, and 8 are building blocks used in...

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Scheme 1: Synthesis of IF-DTF ketones 9–12 and dimer 13.

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Scheme 2: Further functionalization of the IF-DTF ketone 11 via Ramirez/Corey–Fuchs dibromo-olefination and K...

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Scheme 3: Coupling of 1,3-dithiole-2-thione building blocks 2 and 3 with fluorenone 5 to afford fluorene-exte...

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Scheme 4: Synthesis of acetylenic scaffolds based on IF-DTF. Conditions: (a) Pd(PPh₃)₂Cl₂, CuI, THF, Et₃N, rt...

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Scheme 5: Synthesis of acetylenic scaffolds with IF as central core. *Not fully characterized due to poor sol...

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Scheme 6: Reduction of IF dione 1 to dihydro-IF 29.

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Figure 3: UV–vis absorption spectra of compounds 4, 9–12, and 15 in PhMe at 25 °C.

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Figure 4: UV–vis absorption spectra of compounds 13, 16, 17, and 30 in CH₂Cl₂ at 25 °C.

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Figure 5: UV–vis absorption spectra of compounds 22, 23, 26, and 27 in CH₂Cl₂ at 25 °C.

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Figure 6: Cyclic voltammograms of compounds 11 (in MeCN), 13 (in CH₂Cl₂), 15 (in MeCN), 16 (in CH₂Cl₂), and 17...

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Figure 7: Comparison of properties of compounds 13 and 17.

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Figure 8: Cyclic voltammograms of compounds 22, 23, 26, and 27 in CH₂Cl₂; supporting electrolyte: 0.1 M Bu₄NPF...

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Figure 9: Radical anion (left), dianion (middle), and radical cation (right) of compound 23; the radical anio...

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Figure 10: ORTEP plots (50% probability) and crystal packing of compounds a) 25, b) 26, and c) 29. The respect...

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Figure 11: Labels of bonds within five-membered ring.

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Published 15 Jan 2024

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