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π‐Extended Hexapyrrolylbenzenes: Exploring Charge‐Transfer Phenomena in Donor‐Acceptor Propellers
Autorzy
Rok wydania
2023
Czasopismo
Numer woluminu
29
Strony
e202302429/1-e202302429/9
DOI
10.1002/chem.202302429
Kolekcja
Język
Angielski
Typ publikacji
Artykuł
A family of propeller-shaped donor-acceptor hexapyrrolylbenzenes (HPBs) were designed and synthesized by sequential nucleophilic substitution of hexafluorobenzene with π-extended pyrroles. In particular, four hybrids were obtained, containing various combinations of electron-rich and electron-poor acenaphthylene-fused pyrroles. Additionally, to probe the efficiency of ortho transfer interactions, a system was designed containing unique donor and acceptor subunits spatially separated with four unfunctionalized pyrroles. DFT calculations showed propeller-shaped geometries of all HPB molecules and separation of frontier molecular orbitals between donor and acceptor subunits. Steady-state and time-resolved photophysical measurements revealed charge-transfer (CT) character of the emission with strong positive dependence on solvent polarity. The principal CT pathway involves ortho-positioned pairs of donors and acceptors and requires bending of the acceptor in the excited state.
Słowa kluczowe
chromophores, charge transfer, computational chemistry, nucleophilic aromatic substitution, pyrroles
Adres publiczny
http://dx.doi.org/10.1002/chem.202302429
Strona internetowa wydawcy
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