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Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

Yuuki Ishii, Minoru Yamaji, Fumito Tani, Kenta Goto, Yoshihiro Kubozono and Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679. https://doi.org/10.3762/bjoc.21.53

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Supporting Information File 1: Excitation spectra of the fluorescence, synthetic procedures and physical data for the new compounds, theoretical calculation results, copy of ¹H and ¹³C NMR spectra of the prepared compounds.
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Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra

Yuuki Ishii, Minoru Yamaji, Fumito Tani, Kenta Goto, Yoshihiro Kubozono and Hideki Okamoto

Beilstein J. Org. Chem. 2025, 21, 670–679. https://doi.org/10.3762/bjoc.21.53

How to Cite

Ishii, Y.; Yamaji, M.; Tani, F.; Goto, K.; Kubozono, Y.; Okamoto, H. Beilstein J. Org. Chem. 2025, 21, 670–679. doi:10.3762/bjoc.21.53

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TY  - JOUR
A1  - Ishii, Yuuki
A1  - Yamaji, Minoru
A1  - Tani, Fumito
A1  - Goto, Kenta
A1  - Kubozono, Yoshihiro
A1  - Okamoto, Hideki
T1  - Photochemically assisted synthesis of phenacenes fluorinated at the terminal benzene rings and their electronic spectra
JF  - Beilstein Journal of Organic Chemistry
PY  - 2025///
VL  - 21
SP  - 670
EP  - 679
SN  - 1860-5397
DO  - 10.3762/bjoc.21.53
PB  - Beilstein-Institut
JA  - Beilstein J. Org. Chem.
UR  - https://doi.org/10.3762/bjoc.21.53
KW  - fluorescence
KW  - fluorinated aromatics
KW  - phenacene
KW  - photoreaction
N2  - [n]Phenacenes ([n] = 5–7), octafluorinated at the terminal benzene rings (F8-phenacenes: F8PIC, F8FUL, and F87PHEN), were photochemically synthesized, and their electronic spectra were investigated to reveal the effects of the fluorination on the electronic features of phenacene molecules. F8-Phenacenes were conveniently synthesized by the Mallory photoreaction of the corresponding fluorinated diarylethenes as the key step. Upon fluorination on the phenacene cores, the absorption and fluorescence bands of the F8-phenacenes in CHCl3 systematically red-shifted by ca. 3–5 nm compared to those of the corresponding parent phenacenes. The vibrational progressions of the absorption and fluorescence bands were little affected by the fluorination in the solution phase. In the solid state, the absorption band of F8-phenacenes appeared in the similar wavelength region for the corresponding parent phenacenes whereas their fluorescence bands markedly red-shifted and broadened. These observations suggest that the intermolecular interactions of excited-state F8-phenacene molecules are significantly different from those of the corresponding parent molecules, most likely due to different crystalline packing motifs.
ER  -

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aromatic	the word “aromatic”
aromatic aldehyde	the word “aromatic” OR “aldehyde”
+aromatic +aldehyde	both words “aromatic” AND “aldehyde”
+aromatic -aldehyde	the word “aromatic” but NOT “aldehyde”
“aromatic aldehyde”	the exact phrase “aromatic aldehyde”
benz*	words which begin with “benz”, such as “benzene” or “benzyl”
benz*yl	words that begin with “benz” and end with “yl”, such as “benzyl” or “benzoyl”
benzyl~	words that are close to the word “benzyl”, such as “benzoyl” (i.e., fuzzy search)