{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Krzeszewski M"],"funding":["Fundacja na rzecz Nauki Polskiej","Narodowe Centrum Nauki"],"pagination":["2353-2360"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9977460"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["14(9)"],"pubmed_abstract":["A saddle-shaped aza-nanographene containing a central 1,4-dihydropyrrolo[3,2-<i>b</i>]pyrrole (DHPP) has been prepared <i>via</i> a rationally designed four-step synthetic pathway encompassing intramolecular direct arylation, the Scholl reaction, and finally photo-induced radical cyclization. The target non-alternant, nitrogen-embedded polycyclic aromatic hydrocarbon (PAH) incorporates two abutting pentagons between four adjacent heptagons forming unique 7-7-5-5-7-7 topology. Such a combination of odd-membered-ring defects entails a negative Gaussian curvature within its surface with a significant distortion from planarity (saddle height ≈ 4.3 Å). Its absorption and fluorescence maxima are located in the orange-red region, with weak emission originating from the intramolecular charge-transfer character of a low-energy absorption band. Cyclic voltammetry measurements revealed that this stable under ambient conditions aza-nanographene underwent three fully reversible oxidation steps (two one-electron followed by one two-electron) with an exceptionally low first oxidation potential of <i>E</i> <sub>ox1</sub> = -0.38 V (<i>vs.</i> Fc/Fc<sup>+</sup>)."],"journal":["Chemical science"],"pubmed_title":["Saddle-shaped aza-nanographene with multiple odd-membered rings."],"pmcid":["PMC9977460"],"funding_grant_id":["START scholarship no. 039.2017","TEAM POIR.04.04.00-00-3CF4/16-00","HARMONIA 2018/30/M/ST5/00460"],"pubmed_authors":["Dobrzycki L","Gryko DT","Krzeszewski M","Sobolewski AL","Cyranski MK"],"additional_accession":[]},"is_claimable":false,"name":"Saddle-shaped aza-nanographene with multiple odd-membered rings.","description":"A saddle-shaped aza-nanographene containing a central 1,4-dihydropyrrolo[3,2-<i>b</i>]pyrrole (DHPP) has been prepared <i>via</i> a rationally designed four-step synthetic pathway encompassing intramolecular direct arylation, the Scholl reaction, and finally photo-induced radical cyclization. The target non-alternant, nitrogen-embedded polycyclic aromatic hydrocarbon (PAH) incorporates two abutting pentagons between four adjacent heptagons forming unique 7-7-5-5-7-7 topology. Such a combination of odd-membered-ring defects entails a negative Gaussian curvature within its surface with a significant distortion from planarity (saddle height ≈ 4.3 Å). Its absorption and fluorescence maxima are located in the orange-red region, with weak emission originating from the intramolecular charge-transfer character of a low-energy absorption band. Cyclic voltammetry measurements revealed that this stable under ambient conditions aza-nanographene underwent three fully reversible oxidation steps (two one-electron followed by one two-electron) with an exceptionally low first oxidation potential of <i>E</i> <sub>ox1</sub> = -0.38 V (<i>vs.</i> Fc/Fc<sup>+</sup>).","dates":{"release":"2023-01-01T00:00:00Z","publication":"2023 Mar","modification":"2026-03-17T16:00:07.788Z","creation":"2025-02-19T02:21:37.721Z"},"accession":"S-EPMC9977460","cross_references":{"pubmed":["36873850"],"doi":["10.1039/d2sc05858h"]}}