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2 article(s) from Aratani, Naoki

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

Aissam Okba,
Pablo Simón Marqués,
Kyohei Matsuo,
Naoki Aratani,
Hiroko Yamada,
Gwénaël Rapenne and
Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

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Scheme 1: “Precursor approach” for the synthesis of π-conjugated polycyclic compounds, with the thermally- or...

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Scheme 2: Valence isomerization of chalcogen heteropines and subsequent cheletropic extrusion in the case of ...

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Scheme 3: Early example of phenanthrene synthesis via a chemically-induced S-extrusion (and concomitant decar...

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Scheme 4: Top: Conversion of dinaphthothiepine bisimides 3a,b and their sulfoxide analogues 4a,b into PBIs 6a,...

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Figure 1: Top view (a) and side view (b) of the X-ray crystal structure of thiepine 3b showing its bent confo...

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Scheme 5: Modular synthetic route towards dinaphthothiepines 3a–f and the corresponding S-oxides 4a–d, incorp...

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Scheme 6: Top: Conversion of dithienobenzothiepine monomeric units into dithienonaphthalenes, upon S-extrusio...

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Scheme 7: Synthesis of S-doped extended triphenylene derivative 22 from 3-bromothiophene (17) with the therma...

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Scheme 8: Top: Synthesis of thermally-stable O-doped HBC 26a. Bottom: Synthesis of S- and Se-based soluble pr...

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Scheme 9: Synthesis of dinaphthooxepine bisimide 33 and conversion into PBI 6f by O-extrusion triggered by el...

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Figure 2: Cyclic voltammogram of dinaphthooxepine 33, evidencing the irreversibility of the reduction process...

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Scheme 10: Top: Early example of 6-membered ring contraction with concomitant S-extrusion leading to dinaphtho...

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Scheme 11: Examples of S-extrusion from annelated 1,2-dithiins under photoactivation (top) or thermal activati...

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Scheme 12: Synthesis of dibenzo[1,4]dithiapentalene upon photoextrusion of SO₂ [78].

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Scheme 13: Extrusion of SO in naphthotrithiin-2-oxides for the synthesis of 2,5-dihydrothiophene 1-oxides [79].

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Scheme 14: SO-extrusion as a key step in the synthesis of fullerenes (C₆₀ and C₇₀) encapsulating H₂ molecules [80,82]....

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Scheme 15: Synthesis of diepoxytetracene precursor 56 and its on-surface conversion into tetracene upon O-extr...

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Scheme 16: Soluble precursors of hexacene, decacene and dodecacene incorporating 1,4-epoxides in their hydroca...

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Scheme 17: Synthesis of tetraepoxide 59 as soluble precursor of decacene [85].

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Figure 3: Constant-height STM measurement of decacene on Au(111) using a CO-functionalized tip (sample voltag...

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Review

Published 15 Feb 2024

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Direct borylation of terrylene and quaterrylene

Haruka Kano,
Keiji Uehara,
Kyohei Matsuo,
Hironobu Hayashi,
Hiroko Yamada and
Naoki Aratani

Beilstein J. Org. Chem. 2020, 16, 621–627, doi:10.3762/bjoc.16.58

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Figure 1: Chemical structures of a) oligorylene-bisimides, b) oligorylenes, c) bay-bridging oligorylenes, d) ...

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Scheme 1: Synthesis of 2,5,10,13-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)terrylene (TB4): (a) (B...

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Figure 2: (Top) Single crystal X-ray structure of TB4. The thermal ellipsoids are scaled at 50% probability. ...

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Figure 3: UV–vis absorption and fluorescence spectra of terrylene (black) and TB4 (red) in toluene. λ_ex = 489...

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Figure 4: MO diagrams of terrylene and TB4 based on calculations at the B3LYP/6-31G(d).

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Scheme 2: Synthesis of 2,5,12,15-tetrakis(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quaterrylene (QB4): (a)...

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Figure 5: UV–vis absorption spectrum of QB4 in toluene.

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Figure 6: MO diagrams of terrylene and QB4 based on calculations at the B3LYP/6-31G(d).

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Scheme 3: Suzuki–Miyaura cross-coupling reaction of TB4 with 2-bromomesitylene. (a) 2-bromomesitylene (8 equi...

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Letter

Published 06 Apr 2020

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