Precisely metal doped nanographenes via a carbaporphyrin approach

Nature Communications, Journal Year: 2025, Volume and Issue: 16(1)

Published: Feb. 11, 2025

Nanographenes, finite models of graphene sheets, are endowed with intriguing optical, electronic, and spintronic features. So-called heteroatom-doping, where one or more carbon is replaced by non-carbon light atoms has been proved effective in tuning the properties nanographenes. Here we extend concept heteroatom nanographene doping to include metal centers. The method employed involves use a dipyrromethene fragment as an auxiliary ligand that directly linked bay area model hexa-peri-hexabenzocoronene (HBC) give dipyrromethene-fused nanographene-type hybrid (HBCP). HBCP corrole-like trianionic core capable coordinating group 11 cations, including trivalent Cu, Ag Au. These cations introduced into cavity atomic precision complexes (HBCP-M; M = Ag, Au). electronic structure photophysical its investigated steady-state fs-transient spectroscopies, well DFT calculations. also characterized via single crystal X-ray diffraction analyses. This work paves way towards precise nanographenes within network, opposed synthetic appendage independent chelating group, such fused tetrapyrrolic moiety. features which can be tuned replacing heteroatom-doping. authors

Language: Английский

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Base-Catalyzed Chalcogenative Annulation of N-Maleimido O-Aminobenzyl Alcohol with Elemental Sulfur/Selenium: Access to 1,4-Sulfa-/Selena-zepanes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: Feb. 17, 2025

We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing wide scope structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 74–86% and 1,4-thiazines (6 31–68% yields). The characteristics this transformation are high atomic economy, formation two C–Se or C–S bonds in one step, avoiding the use unstable toxic reagents under mild conditions.

Language: Английский

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Chiral nanographenes exhibiting circularly polarized luminescence

Chemical Society Reviews, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

Chiral nanographenes: molecular architecture, key constituents, and their circularly polarized luminescence.

Language: Английский

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Azulene-Fused seco-Hexabenzocoronene-Based Nanographenes

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: April 14, 2025

Due to the unique electronic structure, azulene-containing polycyclic aromatic hydrocarbons attract significant attention toward tuning chemical and properties of benzenoid carbocyclic systems. Here, we report synthesis two types azulene fused, seco-hexabenzocoronene-based nanographenes. The X-ray crystallographic analysis indicated their nonplanar structures with highly torsional periphery in solid structures. typical narrow highest occupied molecular orbital-lowest unoccupied orbital (HOMO-LUMO) energy gaps, long-wavelength absorption, anti-Kasha emissions were investigated by experimental computational studies. Interestingly, these nanographenes exhibited a pronounced photothermal effect.

Language: Английский

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Precise Internal Postsynthetic Oxygen-Doping of Metallonanographenes

Precision Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: May 21, 2025

Language: Английский

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Multi-heteroatom doped nanographenes: enhancing photosensitization capacity by forming an electron donor–acceptor architecture

Chemical Science, Journal Year: 2024, Volume and Issue: 15(29), P. 11408 - 11417

Published: Jan. 1, 2024

A series of multi-heteroatom-doped nanographenes possessing a donor–acceptor architecture were reported.

Language: Английский

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Straightforward Synthesis of Pentagon‐Embedded Expanded [11]Helicenes for Radiative Cooling Property

Chemistry - A European Journal, Journal Year: 2023, Volume and Issue: 30(3)

Published: Oct. 23, 2023

Two new pentagon-embedded carbo[11]helicenes have been designed and synthesized in a three-step process, which are the first example of through post-functionalization twistacene. TD-DFT analyses indicate that both them possess high enantiomerization barriers 42.29 kcal/mol 40.76 kcal/mol, respectively. They emit strong red fluorescence can be chemically oxidized into stable cationic radicals upon addition AgSbF

Language: Английский

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Coumarin-embedded [5]helicene derivatives: synthesis, X-ray analysis and photoconducting properties

Nanoscale, Journal Year: 2024, Volume and Issue: 16(10), P. 5395 - 5400

Published: Jan. 1, 2024

Two novel coumarin-embedded π-extended [5]helicene derivatives (3a and 6a) have been strategically synthesized characterized, the structure of 3a was determined via single crystal X-ray analysis.

Language: Английский

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

Beilstein Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 20, P. 287 - 305

Published: Feb. 15, 2024

The “ precursor approach ” has proved particularly valuable for the preparation of insoluble and unstable π-conjugated polycyclic compounds (π-CPCs), which cannot be synthesized via in-solution organic chemistry, their improved processing, as well electronic investigation both at material single-molecule scales. This method relies on synthesis processing soluble stable direct precursors target π-CPCs, followed by final conversion in situ, triggered thermal activation, photoirradiation or redox control. Beside well-established reactions involving elimination carbon-based small molecules, i.e., retro-Diels–Alder decarbonylation processes, late-stage extrusion chalcogen fragments emerged a highly promising synthetic tool to access wider variety structures thus expand potentialities further improvements molecular materials’ performances. review gives an overview strategies towards π-CPCs ultimate upon electron exchange.

Language: Английский

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Unveiling Energy Transfer Mechanisms in Nanographene-Incorporated Metal–Organic Frameworks

ACS Materials Letters, Journal Year: 2024, Volume and Issue: 6(4), P. 1151 - 1159

Published: Feb. 26, 2024

Nanographenes are a class of extended π-conjugated molecules with great potential for photophysical and electrochemical properties. However, most nanographenes show self-aggregation due to their strong π–π interaction, resulting in structures barely possessing any open π surface. We find that metal–organic frameworks (MOFs) can be an ideal platform construct periodic arrays pores isolated large surfaces by avoiding undesired interactions between the nanographene molecules. Here, we report multivariate series nanographene-incorporated MOFs, UMOF-2-X, utilizing graphene-like hexatopic organic linkers, hexaphenylethynylbenzene (HPB) hexabenzocoronene (HBC), through mixed-linker strategy. Remarkably, UMOF-2 inhibits occurrence linker-to-metal charge transfer Cu metal shows efficient energy HPB HBC linkers.

Language: Английский

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