Doubling the Length of the Longest Pyrene‐Pyrazinoquinoxaline Molecular Nanoribbons

Hernández-Culebras, Félix; Melle‐Franco, Manuel; Mateo‐Alonso, Aurelio

doi:10.1002/anie.202205018

Cited by 28 publications

(19 citation statements)

References 74 publications

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“…Nowadays, the length of pyrene-pyrazinoquinoxaline nanoribbons has been extended to 14.9 nm with 60 aromatic rings in the backbone. 225 Fig. 13 Chemical structures of EWG containing materials.…”

Section: Developed a Dpp-dpp-based Conjugatedmentioning

confidence: 99%

Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications

et al. 2023

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Section: Developed a Dpp-dpp-based Conjugatedmentioning

confidence: 99%

Recent advances in n-type and ambipolar organic semiconductors and their multi-functional applications

et al. 2023

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“…., n - m )- peri -acenoacenes (i.e., also known as benzo[ c ]acenoacenes or trapeziumenes). Generally, the substitution of the carbon edges with heteroatoms has provided a viable approach to prepare zigzag nanographenes, and noticeable examples include O-, − BO-, , OBO-, − B/N-, − NBN-, ,− and BNB-doped , structures. For example, a few years ago, our group reported the first stable (2,7)- peri -acenoacene congener, in which six carbon atoms at the zigzag edges have been replaced by O atoms (Figure b).…”

Section: Introductionmentioning

confidence: 99%

peri-Acenoacene Ribbons with Zigzag BN-Doped Peripheries

et al. 2022

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Here, we report the synthesis of BN-doped graphenoid nanoribbons, in which peripheral carbon atoms at the zigzag edges have been selectively replaced by boron and nitrogen atoms as BN and NBN motifs. This includes high-yielding ring closure key steps that, through N-directed borylation reaction using solely BBr3, allow the planarization of meta-oligoarylenyl precursors, through the formation of B–N and B–C bonds, to give ter-, quater-, quinque-, and sexi-arylenyl nanoribbons. X-ray single-crystal diffraction studies confirmed the formation of the BN and NBN motifs and the zigzag-edged topology of the regularly doped ribbons. Steady-state absorption and emission investigations at room temperature showed a systematic bathochromic shift of the UV–vis absorption and emission envelopes upon elongation of the oligoarylenyl backbone, with the nanoribbon emission featuring a TADF component. All derivatives displayed phosphorescence at 77 K. Electrochemical studies showed that the π-extension of the peri-acenoacene framework provokes a lowering of the first oxidative event (from 0.83 to 0.40 V), making these nanoribbons optimal candidates to engineer p-type organic semiconductors.

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“…The use of molecular nanographenes as gelators can potentially increase the performance of π-gels because of their larger π-surfaces. Even if there has been an increasing effort in the synthesis of giant nanographenes with >150 atoms in their aromatic core, 3 current state-of-the-art nanographene gelators are constituted of C 24 (ref. 4 ) and C 68 (ref.…”

Section: Introductionmentioning

confidence: 99%