Push‐Pull Bridged Distyrylbenzene with Highly Bright Solid‐State Red‐Orange Aggregation‐Induced Emission

Abstract: Multiple emission colors in solid‐state organic fluorophores with the same main skeleton are essential for improving the performance of light‐emitting devices/materials. Specifically, emission in the red/near‐infrared region is of great importance in the biological field. Previously, we developed di‐bridged‐distyrylbenzene DBDB[7] with high‐brightness solid‐state blue and aggregation‐induced emissions (AIE) by introducing the bridging structures of a seven‐membered ring into the vinylene groups of distyrylbenzene (DSB). Herein, we synthesize MNDBDMeODB[7] (1), which features substituted methoxy and malononitrile groups as donor and acceptor groups, respectively, in DBDB[7]. In solvents more polar than THF, MNDSDMeOB (3), which has the same main skeleton as 1 but without bridges, shows no emission in the solid state, whereas 1 exhibits highly bright red‐orange emission in the solid state owing to the suppression of intermolecular electronic interactions by the bridges and the AIE property. We also synthesize MNDSD (EHO) B (2) in which the methoxy groups of 3 are replaced by ethylhexyloxy groups, thus disrupting the crystallinity of the molecule. 2 exhibits positive fluorescence solvatochromism and has a high fluorescence quantum yield in the solid state as a red‐emitting DSB derivative. The solid‐state emission properties of 1 and 2 will improve the applicability of DSBs and functionalities of light‐emitting devices/materials.

Object Details

• Location: Deutsche Nationalbibliothek Frankfurt am Main
• Extent: Online-Ressource
• Language: Englisch

References and Relationships

• Bibliographic citation: Push‐Pull Bridged Distyrylbenzene with Highly Bright Solid‐State Red‐Orange Aggregation‐Induced Emission ; day:19 ; month:06 ; year:2023 ; extent:11 ; Chemistry - a European journal ; (19.06.2023) (gesamt 11)

Contributors, Places and Time

• Creator: Shimomura, Yoshimichi ; Konishi, Gen‐ichi

Further information

• DOI: 10.1002/chem.202301191
• URN: urn:nbn:de:101:1-2023061915143561796493
• Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
• Last update: 14.08.2025, 11:02 AM CEST