Diindeno-Fused Dibenzo[a,h]anthracene and Dibenzo[c,l]chrysene: Syntheses,Structural Analyses,and Properties |
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Authors: | Dr Siva Senthil Kumar Boominathan Kai-Hsin Chang Dr Yu-Chiao Liu Chi-Shin Wang Cheng-Feng Wu Dr Ming-Hsi Chiang Prof Pi-Tai Chou Prof Yao-Ting Wu |
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Institution: | 1. Department of Chemistry, National Cheng Kung University, 70101 Tainan, Taiwan;2. Department of Chemistry, National (Taiwan) University, 10617 Taipei, Taiwan;3. Institute of Chemistry, Academia Sinica, 11529 Taipei, Taiwan |
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Abstract: | Diindeno-fused dibenzoa,h]anthracene 6 and diindeno-fused dibenzoc,l]chrysene 9 contain the key moieties 1,4-quinodipropene (1,4-QDP) and 2,6-naphthoquinodipropene (2,6-NQDP), respectively, and they both have an open-shell singlet ground state. The latter compound exhibits a strong biradical character and interesting properties, including a low ΔET−S (2.44 kcal mol−1), a small HOMO–LUMO gap (1.06 eV), a wide photoabsorption range (250–1172 nm), and a large two-photon absorption cross-section (σ=1342±56 GM). This work verifies that 6 has a slightly larger HOMO–LUMO gap and ΔET−S than its helical isomer diindeno2,1-f:1′,2′-j]picene (DIP), but is a much stronger two-photon absorber, verifying the important effect of geometry on the photophysical properties. |
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Keywords: | aromaticity biradicals naphthoquinodipropene polyarenes quinodipropene |
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