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Paper | Special issue | Vol 101, No. 2, 2020, pp.536-547
Published online, 7th October, 2019
DOI: 10.3987/COM-19-S(F)44
Synthesis and Optical Properties of L-Shaped Dinaphthofluoresceins with Two Peripheral Hydroxy Groups

Hikari Yamashita, Chihiro Minari, Eriko Azuma, Kouji Kuramochi, Ayumi Imayoshi, and Kazunori Tsubaki*

*Graduate School of Life and Environmental Sciences, Kyoto Prefectural University, Shimogamo, Sakyo-ku, Kyoto 606-8522, Japan


The four compounds 6 and 810 having the same L-shaped dinaphthofluorescein skeleton were constructed. The only structural differences among these four compounds were the positions of the two peripheral hydroxy groups. Their dianion forms are a resonance system, thus 6 and 810 were expected to exhibit similar optical properties such as the maximum absorption wavelength, molar absorptivity, maximum emission wavelength and fluorescence quantum yield. However, 6 and 810 showed quite different optical properties. For example, the maximum absorption wavelengths of 6, 8, 9 and 10 in aqueous pH 11 solution were 650 nm, 733 nm, 558 nm and 746 nm, respectively. Thus, the positions of the two peripheral hydroxy groups on the same skeleton significantly affected the optical properties.