Synthesis and Photophysical Studies of Naphthalene Diimide-based[3]Rotaxanes
Received date: 2018-07-04
Online published: 2018-08-13
Supported by
Project supported by the National Natural Science Foundation of China (Nos. 21525206, 21561130149 and 21474124) and the Newton Advanced Fellowship.
Rotaxanes, composed of macrocyclic wheel and linear axle, have been used in areas such as molecular machines, stimuli-responsive materials, information storage, supramolecular catalysts. The macrocyclic host and its noncovalent interaction are key for the rotaxanes. Pillar[n]arenes (n=5~10) have drew much attention as widely-used hosts. Their facile synthesis, unique rigid structure, versatile functionalization, and interesting host-guest properties enable pillar[n]arenes to build various supramolecular architectures including rotaxanes. Currently, the research of pillararene-based rotaxanes mainly focuses on the synthesis, the responsiveness to temperature and solvent, and the application as catalyst, however, reports of emissive pillararene-based rotaxanes are very rare. Besides, higher-ordered[n]rotaxanes (n ≥ 3) based on pillararene remain rarely explored limited by the poor synthetic yield, despite their fascinating structure and potential applications in molecular devices. Herein, we report two pillararene-based rotaxanes ([3]R and [3]R') incorporating naphthalene diimide with red fluorescence in solid state. The 1,4-diethoxypillar[5]arene (EtP5A) was chosen as the wheel, diamino-substituted naphthalene diimides (NDI) were used as the axle containing two separated linear guest parts for EtP5A. The addition reaction of NDI-precursor S1/S2 and the stopper 3,5-dimethylphenyl isocyanate with the presence of EtP5A afforded [3]R and[2]R (byproduct as model compound)/[3]R', respectively, with high yield of 45% for [3]R and 62% for [3]R'. The structures of rotaxanes were confirmed by 1H NMR spectroscopy, ROESY (rotating frame Overhause enhancement spectroscopy), and HR-ESI-MS. Limited by the length of linear chains, EtP5As are adjacent tightly to NDI in [3]R, whereas EtP5As stay four-atom distance away from NDI in 3[R]'. The optical properties of rotaxanes in various solvents and in powders were detected. [3]R and [3]R' show bright red fluorescence not only in solution but also in solid state, which distinguishes [3]R and [3]R' from [2]R and most of NDI-based fluorescent compounds. The increased fluorescence in solid state of [3]R and [3]R' benefits from the bulky EtP5As hindering the π-π interaction and suppressing the self-quenching of NDI. We suspect that [3]R and [3]R' may have potential applications in red-emitting materials and optoelectronic devices.
Key words： rotaxane; pillararene; fluorescence; naphthalene diimide
Sun Cai-Li , Teng Kun-Xu , Niu Li-Ya , Chen Yu-Zhe , Yang Qing-Zheng . Synthesis and Photophysical Studies of Naphthalene Diimide-based[3]Rotaxanes[J]. Acta Chimica Sinica, 2018 , 76(10) : 779 -784 . DOI: 10.6023/A18070258
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