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Chemical Structure| 26465-81-6

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Górski, Krzysztof ; Pejov, Ljupcho ; Jørgensen, Kåre B ; Knysh, Iryna ; Jacquemin, Denis ; Gryko, Daniel T

Abstract: Here we present a highly versatile synthetic strategy based on twofold 6π-electrocyclization accompanied with HBr elimination as a novel approach towards centrosymmetric multi-heteroatom-doped nanographenes build around an electron-rich 1,4-dihydropyrrolo[3,2-b]pyrrole core. A straightforward synthesis from readily available substrates offers a unique possibility of fusing the 1,4-dihydropyrrolo[3,2-b]pyrrole subunit not only with carbocyclic building blocks, such as electron-deficient phenanthrenes, chrysenes, or [4]helicenes, but also with heterocyclic systems, such asbenzo[b]furan and 5-thiatruxene. The clear advantage of this strategy is that there is no requirement to assemble complex scaffolds possessing bromoaryl units since bromine atom is introduced by bromination of 1,4-dihydropyrrolo[3,2-b]pyrrole core which, because of its exceptionally electron-rich character, is straightforward reaction. The obtained χ-shaped and S-shaped nanographenes containing 10or more fused rings, exhibit visible-range emissions characterized by fluorescence quantum yields reaching 48%. Computational studies of the reaction mechanism revealed that the 6π-electrocyclization is kinetically favourable over photo-induced direct arylation. Steadystate UV/Visible spectroscopy reveals that upon photoexcitation, the prepared S-shaped N-doped nanographenes undergo mostly radiative relaxation leading to large fluorescence quantum yields. We anticipate that this chemistry will empower the creation of new materials with various functionalities.

Keywords: Dyes/Pigments ; Photochemistry ; Nanographenes ; Pyrrole ; Fluorescence

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Product Details of [ 26465-81-6 ]

CAS No. :26465-81-6
Formula : C11H12O
M.W : 160.21
SMILES Code : CC1(C)CC(=O)C2=CC=CC=C12
MDL No. :MFCD01846169
InChI Key :QWZAOSKLFKAEOK-UHFFFAOYSA-N
Pubchem ID :304628

Safety of [ 26465-81-6 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338
 

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