Oxa[7]superhelicene: A π‐Extended Helical Chromophore Based on Hexa‐<i>peri</i>‐hexabenzocoronenes

Reger, David; Haines, Philipp; Heinemann, Frank W.; Guldi, Dirk M.; Jux, Norbert

doi:10.1002/anie.201800585

Cited by 103 publications

(81 citation statements)

References 57 publications

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“…First, mono‐porphyrin‐HBC 6 , previously made by us through a different route, was prepared as a reference compound (Scheme ). For this purpose, mono‐porphyrin‐tolane 1 was synthesized in a literature‐known statistical porphyrin condensation and reacted with tetracyclone 2 to the mono‐porphyrin‐HPB 3 . The transformation to the respective HBC derivative 6 worked almost quantitatively using FeCl 3 as the oxidant.…”

Section: Resultsmentioning

confidence: 99%

“…Scheme1.Synthesis of mono-and tri-porphyrin-HBCs 6, 7,and 8.Molecules 3, 4,and 6 are depicted as X-ray crystal structures (for details see the Supporting Information). [45] a) Ph 2 O, 260 8C, mW; b) Ni(acac) 2 ,toluene, 110 8C; c) Co 2 (CO) 8 [31] was synthesized in al iterature-known statistical porphyrin condensation and reactedw ith tetracyclone 2 [40,42] to the mono-porphyrin-HPB 3. [31,38] The transformation to the respective HBC derivative 6 workeda lmost quantitatively using FeCl 3 as the oxidant.…”

Section: Resultsmentioning

confidence: 99%

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Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Martin

Lungerich

Hampel

et al. 2019

Chemistry A European J

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Porphyrin–hexabenzocoronene architectures serve as good model compounds to study light‐harvesting systems. Herein, the synthesis of porphyrin functionalized hexa‐peri‐hexabenzocoronenes (HBCs), in which one or more porphyrins are covalently linked to a central HBC core, is presented. A series of hexaphenylbenzenes (HPBs) was prepared and reacted under oxidative coupling conditions. The transformation to the respective HBC derivatives worked well with mono‐ and tri‐porphyrin‐substituted HPBs. However, if more porphyrins are attached to the HPB core, Scholl oxidations are hampered or completely suppressed. Hence, a change of the synthetic strategy was necessary to first preform the HBC core, followed by the introduction of the porphyrins. All products were fully characterized, including, if possible, single‐crystal XRD. UV/Vis absorption spectra of porphyrin‐HBCs showed, depending on the number of porphyrins as well as with respect to the substitution pattern, variations in their spectral features with strong distortions of the porphyrins’ B‐band.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Martin

Lungerich

Hampel

et al. 2019

Chemistry A European J

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“…Compound 206 was synthesized by Jux and co‐workers using DDQ/TfOH to oxidatively close 13 new C aryl –C aryl bonds in one operation (Figure ) . 206 consists of two penta( tert ‐butyl‐HBC) units fused to a central furan core, hence, forming an oxa[7]helicene derivative.…”

Section: Intramolecular Oxidative Aromatic Couplingmentioning

confidence: 99%

“…Ther emaining three compounds presented in Figure 17 (206)(207)(208)w ere all reported in 2018 and belong to the class known as "superhelicenes", aterm coined for unusually large Compound 206 was synthesized by Juxa nd co-workers using DDQ/TfOH to oxidatively close 13 new C aryl -C aryl bonds in one operation (Figure 17). [236] 206 consists of two penta(tert-butyl-HBC) units fused to ac entral furan core, hence,forming an oxa [7]helicene derivative.Replacing DDQ by FeCl 3 as an oxidant leads to the non-fully cyclized bis-HBC ether (lacking the furan ring) which, however,readily cyclizes to 206 upon exposure to light.…”

Section: Curved Twisted and Strained Structuresmentioning

confidence: 99%

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

et al. 2019

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Oxidative aromatic coupling occupies a fundamental place in the modern chemistry of aromatic compounds. It is a method of choice for the assembly of large and bewildering architectures. Considerable effort was also devoted to applications of the Scholl reaction for the synthesis of chiral biphenols and natural products. The ability to form biaryl linkages without any prefunctionalization provides an efficient pathway to many complex structures. Although the chemistry of this process is only now becoming fully understood, this reaction continues to both fascinate and challenge researchers. This is especially true for heterocoupling, that is, oxidative aromatic coupling with the chemoselective formation of a C−C bond between two different arenes. Analysis of the progress achieved in this field since 2013 reveals that many groups have contributed by pushing the boundary of structural possibilities, expanding into surface‐assisted (cyclo)dehydrogenation, and developing new reagents.

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“…Tetrakis-(4-(tert-butyl)phenyl)cyclopentadienone (9) was synthesized according to literature procedures. [1], [2], [3]…”

Section: Tetrakis-(4-(tert-butyl)phenyl)cyclopentadienone (9)mentioning

confidence: 99%

Synthesis and Photophysical Properties of Hexaphenylbenzene–Pyrrolo[3,2-b]pyrroles

Stężycki

Reger

Hoelzel

et al. 2018

Synlett

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Methods for the synthesis of pyrrolo[3,2-b]pyrroles containing hexaphenylbenzene moieties at the 2- and 5-positions or the 1- and 4-positions have been developed. It was shown that placing a hexaphenylbenzene moiety at the 2- and 5-positions requires a Diels–Alder reaction between an alkyne-substituted pyrrolopyrrole core and a 2,3,4,5-tetraphenylcyclopenta-2,4-dien-1-one. The resulting dyes show a strong blue fluorescence that was hypsochromically shifted by chlorination at the 3- and 6-positions. The overall conjugation between the hexaphenylbenzene moieties and the pyrrolopyrrole core is limited, as evident from their photophysical properties. The hexaphenylbenzene moieties attached to the pyrrolo[3,2-b]pyrrole core could not be transformed into hexa-peri-hexabenzocoronenes through intramolecular oxidative aromatic coupling.

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Oxa[7]superhelicene: A π‐Extended Helical Chromophore Based on Hexa‐peri‐hexabenzocoronenes

Cited by 103 publications

References 57 publications

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Multiple‐Porphyrin Functionalized Hexabenzocoronenes

Synthetic Applications of Oxidative Aromatic Coupling—From Biphenols to Nanographenes

Synthesis and Photophysical Properties of Hexaphenylbenzene–Pyrrolo[3,2-b]pyrroles

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