Vinylpyrroles: solid-state structures and aggregation-induced emission properties

Toru Okawara; Yurina Matsufuji; Kouhei Mizuno; Kenji Takehara; Toshihiko Nagamura; Seiji Iwasa

doi:10.1039/c9ra04088a

Vinylpyrroles: solid-state structures and aggregation-induced emission properties

RSC Adv. 2019 Jul 23;9(40):22817-22822. doi: 10.1039/c9ra04088a.

Authors

Toru Okawara¹, Yurina Matsufuji², Kouhei Mizuno¹, Kenji Takehara¹, Toshihiko Nagamura^{1

3}, Seiji Iwasa⁴

Affiliations

¹ Department of Creative Engineering, National Institute of Technology, Kitakyushu College Shii 5-20-1, Kokuraminami-ku, Kitakyushu Fukuoka 802-0985 Japan okawara@kct.ac.jp.
² Advanced School of Creative Engineering, National Institute of Technology, Kitakyushu College Shii 5-20-1, Kokuraminami-ku, Kitakyushu Fukuoka 802-0985 Japan.
³ Advanced Manufacturing Research Institute Biochemical Process Research Group, National Institute of Advanced Industrial Science and Technology (AIST) 807-1 Shuku-machi, Tosu Saga 841-0052 Japan.
⁴ Department of Applied Chemistry and Life Science, Toyohashi University of Technology 1-1 Tempaku-cho, Toyohashi Aichi 441-8580 Japan.

Abstract

An aggregation-induced emission chromophore, vinylpyrrole, was prepared from a formylpyrrole derivative, Meldrum's acid, and 1,3-dimethylbarbituric acid. The optical properties of the chromophore both in the solution and solid states were investigated by UV-vis and fluorescence spectroscopy. Single crystal X-ray diffraction measurements revealed that the dimethylbarbituric acid adduct formed a J-aggregate in the solid and resulted in higher fluorescence quantum yield compared to the Meldrum's acid adduct. Emission enhancement was found to occur by the restriction of molecular rotation in the solid state.