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Literature DB >> 29039182

Chiral Nanographene Propeller Embedding Six Enantiomerically Stable [5]Helicene Units.

Veronika Berezhnaia¹, Myriam Roy¹, Nicolas Vanthuyne², Marco Villa¹, Jean-Valère Naubron³, Jean Rodriguez², Yoann Coquerel², Marc Gingras¹.

Abstract

A one-step synthesis of a nanographene propeller with a D3-symmetry was obtained starting from 7,8-dibromo[5]helicene by Yamamoto nickel(0) couplings. It afforded a chiral polyaromatic hydrocarbon (PAH) embedding six enantiomerically stable [5]helicene units. This dense accumulation of helical strain resulted in a distorted geometry, but stable stereochemistry. The conformational, structural, chiroptical, and photophysical properties of the molecule are reported.

Entities: Chemical

Year: 2017 PMID： 29039182 DOI： 10.1021/jacs.7b07622

Source DB: PubMed Journal: J Am Chem Soc ISSN： 0002-7863 Impact factor: 15.419

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Cited

7 in total

Review 1. Nanographenes and Graphene Nanoribbons as Multitalents of Present and Future Materials Science.

Authors: Yanwei Gu; Zijie Qiu; Klaus Müllen
Journal: J Am Chem Soc Date: 2022-06-07 Impact factor: 16.383

2. Enantiopure distorted ribbon-shaped nanographene combining two-photon absorption-based upconversion and circularly polarized luminescence.

Authors: Carlos M Cruz; Irene R Márquez; Inês F A Mariz; Victor Blanco; Carlos Sánchez-Sánchez; Jesús M Sobrado; José A Martín-Gago; Juan M Cuerva; Ermelinda Maçôas; Araceli G Campaña
Journal: Chem Sci Date: 2018-03-14 Impact factor: 9.825

3. Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol-diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction.

Authors: Zachary A Kasun; Hiroki Sato; Jing Nie; Yasuyuki Mori; Jon A Bender; Sean T Roberts; Michael J Krische
Journal: Chem Sci Date: 2018-08-30 Impact factor: 9.825

Chiral Nanographene Propeller Embedding Six Enantiomerically Stable [5]Helicene Units.

Review 1. Nanographenes and Graphene Nanoribbons as Multitalents of Present and Future Materials Science.

2. Enantiopure distorted ribbon-shaped nanographene combining two-photon absorption-based upconversion and circularly polarized luminescence.

3. Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol-diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction.

4. Charging OBO-Fused Double [5]Helicene with Electrons.

5. Stereospecific Synthesis and Photophysical Properties of Propeller-Shaped C₉₀ H₄₈ PAH.

6. Preparation of substituted triphenylenes via nickel-mediated Yamamoto coupling.

7. Helicity Modulation in NIR-Absorbing Porphyrin-Ryleneimides.

Chiral Nanographene Propeller Embedding Six Enantiomerically Stable [5]Helicene Units.

Review 1. Nanographenes and Graphene Nanoribbons as Multitalents of Present and Future Materials Science.

2. Enantiopure distorted ribbon-shaped nanographene combining two-photon absorption-based upconversion and circularly polarized luminescence.

3. Alternating oligo(o,p-phenylenes) via ruthenium catalyzed diol-diene benzannulation: orthogonality to cross-coupling enables de novo nanographene and PAH construction.

4. Charging OBO-Fused Double [5]Helicene with Electrons.

5. Stereospecific Synthesis and Photophysical Properties of Propeller-Shaped C90 H48 PAH.

6. Preparation of substituted triphenylenes via nickel-mediated Yamamoto coupling.

7. Helicity Modulation in NIR-Absorbing Porphyrin-Ryleneimides.

5. Stereospecific Synthesis and Photophysical Properties of Propeller-Shaped C₉₀ H₄₈ PAH.