Affiliation:
1. Graduate School of Engineering, University of Hyogo, 2167 Shosha, Himeji, Hyogo 671-2280, Japan.
2. School of Engineering, The University of Shiga Prefecture, 2500, Hassaka-cho, Hikone, Shiga 522-8533, Japan.
Abstract
Diels–Alder reactions of acenaphthylene-5,6-dicarboximide (AI) derivatives with the corresponding dienes afforded some derivatives of π-extended fluoranthene imide, namely N-(2-ethylhexyl)-7,10-diphenylfluoranthene imide (DPFI) and N-(2-ethylhexyl)-7,8,9,10-tetraphenylfluoranthene imide (TPFI), N-(n-octyl)-benzo[k]fluoranthene imide (BFI), and N-(n-octyl)-naphtho[k]fluoranthene imide (NFI). Molecular structures of TPFI and BFI reveal that the core π-skeletons have a highly planar structure, and the molecules form a dimeric structure in the crystals. The absorption spectra exhibit bathochromic shift with π-extension of the core π-skeletons. On the other hand, DPFI and TPFI show the long-wavelength emission related to BFI, probably due to π-extension toward the phenyl substituents in the excited states. BFI and NFI exhibited an interesting concentration-dependent 1H-NMR behavior in CDCl3, suggesting self-aggregation formation. Moreover, BFI and NFI show moderate and remarkable solvatofluorochromism in solutions (BFI for ΔλEM = 67 nm, NFI for ΔλEM = 116 nm), respectively, while DPFI and TPFI show weak solvatofluorochromism. The density functional theory calculations demonstrate that the considerable spatial separation between the HOMO and LUMO coefficients in the NFI molecule. The result indicates that the ground-to-excited state transition of NFI should have intramolecular charge transfer (ICT) character.
Publisher
Canadian Science Publishing
Subject
Organic Chemistry,General Chemistry,Catalysis
Cited by
11 articles.
订阅此论文施引文献
订阅此论文施引文献,注册后可以免费订阅5篇论文的施引文献,订阅后可以查看论文全部施引文献