Development of Yellow-to-Orange Photoluminescence Molecules Based on Alterations in the Donor Units of Fluorinated Tolanes

Author:

Yamada ShigeyukiORCID,Kobayashi Kazuki,Konno Tsutomu

Abstract

Since the aggregation-induced emission (AIE) phenomenon was first reported by Tang et al., much effort has been devoted to the development of solid-state luminescent molecules by chemists worldwide. Our group successfully developed fluorinated tolanes as novel compact π-conjugated luminophores with blue photoluminescence (PL) in the crystalline state. Moreover, we reported the yellow-green PL molecules based on their electron-density distributions. In the present study, we designed and synthesized fluorinated tolanes with various amine-based donors and evaluated their photophysical properties. The carbazole-substituted fluorinated tolane exhibited strong PL in the solution state, whereas piperidine- or phenothiazine-substituted fluorinated tolanes showed a dramatic decrease in PL efficiency. Notably, fluorinated tolanes with piperidine or phenothiazine substituents displayed yellow-to-orange PL in the crystalline state; this may have occurred because these tolanes exhibited tightly packed structures formed by intermolecular interactions, such as H···F hydrogen bonds, which suppressed the non-radiative deactivation process. Moreover, fluorinated tolanes with amine-based donors exhibited AIE characteristics. We believe that these yellow-to-orange solid PL molecules can contribute to the development of new solid luminescent materials.

Funder

Murata Science Foundation

Shorai Foundation For Science And Technology

Publisher

MDPI AG

Subject

Chemistry (miscellaneous),Analytical Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Molecular Medicine,Drug Discovery,Pharmaceutical Science

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