Tuning the Metal-Free Room Temperature Phosphorescence of Fluorene-Based Chromophores through Side-Group Molecular Engineering

IF 7.2 2区材料科学 Q2 CHEMISTRY, PHYSICAL

Chemistry of Materials Pub Date : 2025-02-25 DOI:10.1021/acs.chemmater.4c03482

Maxime Rémond, Hee Jung Kim, Yanghyun Auh, Kwang Keat Leong, Jinbo Kim, Hwandong Jang, Yongnam Ahn, Kiyoung Chang, Eunkyoung Kim

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Abstract

A series of bromofluorene-based metal-free dyes (BrFX) exhibiting room-temperature phosphorescence (RTP) were synthesized via a scalable two-step process in high yields from the linkage of 2-bromofluorene (BrF) through a ketone with different side group (X). Structural analysis of BrFX revealed that the ketone group was well conjugated with the fluorene group but less conjugated with the X side group. The nature of the X side group played a crucial role in fine-tuning emission maxima of BrFX. Moreover, incorporating aromatic side groups having low triplet energy effectively red-shifted RTP and increased its lifetime. Theoretical calculations using density functional theory revealed that the highest occupied molecular orbital was localized on the fluorene core, supporting these experimental observations. BrFX showed strong phosphorescence in diverse amorphous semiconducting hosts with quantum yields up to 65%, enabling their application in light-emitting electrochemical cells. These findings underscore the success of converting BrFH into its ketone analogs, BrFX, as an effective strategy to enhance both phosphorescence and electroluminescence, representing a notable advancement in RTP molecule design.

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来源期刊

Chemistry of Materials 工程技术-材料科学：综合

CiteScore

14.10

自引率

5.80%

发文量

929

审稿时长

1.5 months

期刊介绍： The journal Chemistry of Materials focuses on publishing original research at the intersection of materials science and chemistry. The studies published in the journal involve chemistry as a prominent component and explore topics such as the design, synthesis, characterization, processing, understanding, and application of functional or potentially functional materials. The journal covers various areas of interest, including inorganic and organic solid-state chemistry, nanomaterials, biomaterials, thin films and polymers, and composite/hybrid materials. The journal particularly seeks papers that highlight the creation or development of innovative materials with novel optical, electrical, magnetic, catalytic, or mechanical properties. It is essential that manuscripts on these topics have a primary focus on the chemistry of materials and represent a significant advancement compared to prior research. Before external reviews are sought, submitted manuscripts undergo a review process by a minimum of two editors to ensure their appropriateness for the journal and the presence of sufficient evidence of a significant advance that will be of broad interest to the materials chemistry community.