The chemistry of phenalenium systems XXI. Cyclopenta[cd]phenalenyl anion☆
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Organic molecules with inverted gaps between first excited singlet and triplet states and appreciable fluorescence rates
2021, MatterCitation Excerpt :Before carrying out a more focused investigation toward INVEST molecules with appreciable fluorescence rates, we tested a few modifications of molecules 1 and 2 to find out what structural features would make the singlet-triplet gap positive. One modification of 1 and 2 that preserved the inverted gap, but also blue-shifted the excitation significantly, is the modification leading to azacyclopenta[cd]-phenalene68 18, shown in Scheme 5A. Hence, analogously to before, we explored all structures resulting from systematic permutations of all possible substitutions of C–H with N (Scheme 5B). Figure 5A shows the map of the singlet-triplet gaps and the oscillator strengths at the EOM-CCSD/cc-pVDZ level of theory and Figure 5B shows the map of the singlet-triplet gaps and the vertical excitation energies.
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For Part XX, see I. Murata, K. Nakasuji, K. Yamamoto, T. Nakazawa, Y. Kayane, A. Kimura, and O. Hara, Angew. Chem., in the press (1975).