Gold Catalysis Meets Materials Science – A New Approach to π‐Extended Indolocarbazoles

Hendrich, Christoph M.; Bongartz, Lukas M.; Hoffmann, Marvin; Zschieschang, Ute; Borchert, James W.; Sauter, Désirée; Krämer, Petra; Röminger, Frank; Mulks, Florian F.; Rudolph, Matthias; Dreuw, Andreas; Klauk, Hagen; Hashmi, A. Stephen K.

doi:10.1002/adsc.202001123

Cited by 20 publications

(16 citation statements)

References 54 publications

(18 reference statements)

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“…In a just published article, Hashmi and co-workers extended this bidirectional pathway in an elegant way to aryl-tethered tetraynes. 379 Different substituted alkyne systems 125 were cyclized with 5 mol % of IPrAuNTf 2 to the corresponding Bocprotected π-extended indolocarbazoles 126 in good yields (Scheme 72). After thermal cleavage of the protecting group, the latter was necessary for the synthesis of the tetraynes; the benzo−benzo−indolocarbazoles 127 (BBICZ) could be alkylated to the corresponding 128 in order to keep the systems soluble.…”

Section: Carbazolesmentioning

confidence: 99%

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Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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Often stoichiometric amounts of gold find use in materials science; occasionally gold is even used as a support. This review discusses the contributions of gold catalysis, both homogeneous and heterogeneous, to the field of materials science. One topic is the synthesis of polymers, including nanowires and polyesters, the postcyclization of polymers, polymerization by cyclopropanation, and gold-catalyzed radical polymerization reactions. Other topics are dyes, phosphonium salts, and a wide range of extended conjugated π-systems, the latter ranging from acenes, pentalene derivatives, and different heterocyclic π-systems to fascinating applications in the synthesis of helical anellated aromatic molecules. The existing contributions clearly demonstrate the potential of gold catalysis for significant future impulses for the field of materials science.

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Section: Carbazolesmentioning

confidence: 99%

“…In a just published article, Hashmi and co-workers extended this bidirectional pathway in an elegant way to aryl-tethered tetraynes . Different substituted alkyne systems 125 were cyclized with 5 mol % of IPrAuNTf 2 to the corresponding Boc-protected π-extended indolocarbazoles 126 in good yields (Scheme ).…”

Section: Extended Anellated Aromatic Systemsmentioning

confidence: 99%

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

et al. 2020

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“…To access non-N-arylated para -dipyrrolobenzenes, we followed a reaction procedure recently established in our group that relies on the Boc-protected aniline 5 (Scheme ). The Boc-protected para -dipyrrolobenzene p DPBe′ was obtained in excellent yield (94% in the final step). Heating of the compound to 200 °C led to deprotected p DPBe in almost quantitative yield (98%) and in an overall yield of 86% over three steps, which significantly outperforms previously reported syntheses. − …”

Section: Resultsmentioning

confidence: 99%

Efficient Synthesis of Dipyrrolobenzenes and Dipyrrolopyrazines via Bidirectional Gold Catalysis: a Combined Synthetic and Photophysical Study

et al. 2022

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New N-heterocyclic fluorophores are sought-after compounds for organic electronic devices. Here, we report on a straightforward synthesis to access meta/para-dipyrrolobenzenes and para-dipyrrolopyrazines in high yields using a bidirectional gold-catalyzed cyclization strategy. The versatility of our reaction protocol was showcased by preparing dipyrroloarenes with different substituents, various functional groups, and in a multitude of substitution patterns. Furthermore, we showed that the dipyrroloarenes can be post-modified by N-alkylation to improve the solubility or bromination to yield precursors for further derivatization via cross-coupling. Investigation of the photophysical properties of themostly unprecedenteddipyrroloarenes identified strong blue emitters such as the diphenyl metadipyrrolobenzene with a quantum yield of 98%. Moreover, we showed that changes in the solvent polarity or interactions with Lewis acids such as borane can be used to fine-tune the photophysical properties of the fluorophores.

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“…After optimization of the gold‐catalyzed step we focused on the cleavage of the Boc protecting group. Besides common ways like acid‐mediated deprotection methods, [17] an approach by Cava from 1985, [18] which we had already successfully used for indolocarbazoles [3a] looked promising. This solvent‐free thermal deprotection, originally used for pyrrole‐based substances, was also effective for our Boc‐protected product 6 a .…”

Section: Resultsmentioning

confidence: 99%

“Golden” Cascade Cyclization to Benzo[c]‐Phenanthridines

Hendrich

Senn

Haas

et al. 2021

Chemistry A European J

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Herein, we describe a gold-catalyzed cascade cyclization of Boc-protected benzylamines bearing two tethered alkyne moieties in a domino reaction initiated by a 6endo-dig cyclization. The reaction was screened intensively, and the scope was explored, resulting in nine new Bocprotected dihydrobenzo[c]phenanthridines with yields of up to 98 %; even a π-extension and two bidirectional approaches were successful. Furthermore, thermal cleavage of the Boc group and subsequent oxidation gave substituted benzo [c] phenanthridines in up to quantitative yields. Two bidirectional approaches under the optimized conditions were successful, and the resulting π-extended molecules were tested as organic semiconductors in organic thin-film transistors.

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Gold Catalysis Meets Materials Science – A New Approach to π‐Extended Indolocarbazoles

Cited by 20 publications

References 54 publications

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Homogeneous and Heterogeneous Gold Catalysis for Materials Science

Efficient Synthesis of Dipyrrolobenzenes and Dipyrrolopyrazines via Bidirectional Gold Catalysis: a Combined Synthetic and Photophysical Study

“Golden” Cascade Cyclization to Benzo[c]‐Phenanthridines

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