Fulvalene‐Based Polycyclic Aromatic Hydrocarbon Ladder‐Type Structures: Synthesis and Properties
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Fulvalene‐Based Polycyclic Aromatic Hydrocarbon Ladder‐Type Structures : Synthesis and Properties. / Bliksted Roug Pedersen, Viktor; Granhøj, Jeppe; Erbs Hillers‐bendtsen, Andreas; Kadziola, Anders; Mikkelsen, Kurt V.; Brøndsted Nielsen, Mogens.
In: Chemistry: A European Journal, Vol. 27, No. 32, 2021, p. 8315-8324.Research output: Contribution to journal › Journal article › Research › peer-review
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TY - JOUR
T1 - Fulvalene‐Based Polycyclic Aromatic Hydrocarbon Ladder‐Type Structures
T2 - Synthesis and Properties
AU - Bliksted Roug Pedersen, Viktor
AU - Granhøj, Jeppe
AU - Erbs Hillers‐bendtsen, Andreas
AU - Kadziola, Anders
AU - Mikkelsen, Kurt V.
AU - Brøndsted Nielsen, Mogens
PY - 2021
Y1 - 2021
N2 - Polycyclic aromatic hydrocarbons (PAHs) have found strong interest for their electronic properties and as model systems for graphene. While PAHs have been studied intensively as single units, here PAHs were constructed in ladder-type arrangements using cross-conjugated fulvalene and dithiafulvalene motifs as connecting units and moving forward a convenient synthetic approach for dimerizing (thio)ketones into olefins by the action of Lawesson's reagent. Some of the PAHs can also be regarded as “super-extended” tetrathiafulvalenes (TTFs) with some of the largest cores ever explored, being multi-redox systems that exhibit both reversible oxidations and reductions. Concomitant absorption redshifts were observed when expanding the ladder-type structures from one to two to three indenofluorene units, and optical and electrochemical HOMO-LUMO gaps were found to correlate linearly. Various conformations (and solid-state packing arrangements) were studied by X-ray crystallography and computations.
AB - Polycyclic aromatic hydrocarbons (PAHs) have found strong interest for their electronic properties and as model systems for graphene. While PAHs have been studied intensively as single units, here PAHs were constructed in ladder-type arrangements using cross-conjugated fulvalene and dithiafulvalene motifs as connecting units and moving forward a convenient synthetic approach for dimerizing (thio)ketones into olefins by the action of Lawesson's reagent. Some of the PAHs can also be regarded as “super-extended” tetrathiafulvalenes (TTFs) with some of the largest cores ever explored, being multi-redox systems that exhibit both reversible oxidations and reductions. Concomitant absorption redshifts were observed when expanding the ladder-type structures from one to two to three indenofluorene units, and optical and electrochemical HOMO-LUMO gaps were found to correlate linearly. Various conformations (and solid-state packing arrangements) were studied by X-ray crystallography and computations.
U2 - 10.1002/chem.202100984
DO - 10.1002/chem.202100984
M3 - Journal article
C2 - 33856724
VL - 27
SP - 8315
EP - 8324
JO - Chemistry: A European Journal
JF - Chemistry: A European Journal
SN - 0947-6539
IS - 32
ER -
ID: 269508773