open access

https://hdl.handle.net/2115/91926

Enhancement of NIR-Absorbing Ability of Bis(diarylmethylium)-Type Dicationic Dyes Based on an Ortho-Substitution Strategy.

英語

X-ray analysis

2023-04-21

Wiley-Blackwell

Chemistry-A European journal

29(23)

e202203899

Electrochromic systems capable of switching near-infrared (NIR) absorption are fascinating from the viewpoint of applications in the materials and life sciences. Although 11,11,12,12-tetraaryl-9,10-anthraquinodimethanes (AQDs) with a folded form undergo one-stage two-electron oxidation to produce twisted dicationic dyes exhibiting NIR absorption, there is a need to establish a design strategy that can enhance the NIR-absorbing abilities of the corresponding dicationic dyes. In this study, we designed and synthesized a series of AQD derivatives with various substituents introduced at the ortho-position(s) of the 4-methoxyphenyl group. X-ray and spectroscopic analyses revealed that NIR-absorbing properties can be changed by introduction of the ortho-substituents. Thus, control of the steric and electronic effects of the ortho-substituents on the 4-methoxyphenyl groups was demonstrated to be an effective strategy for fine-tuning of the HOMO and LUMO levels for neutral AQDs and twisted dications, respectively, resulting in the modification of electrochemical and spectroscopic properties under an ortho-substitution strategy.

学術雑誌論文

Accepted Manuscript

This is the peer reviewed version of the following article: Enhancement of NIR-Absorbing Ability of Bis(diarylmethylium)-Type Dicationic Dyes Based on an Ortho-Substitution Strategy. which has been published in final form at https://doi.org/10.1002/chem.202203899. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Use of Self-Archived Versions. This article may not be enhanced, enriched or otherwise transformed into a derivative work, without express permission from Wiley or by statutory rights under applicable legislation. Copyright notices must not be removed, obscured or modified. The article must be linked to Wiley’s version of record on Wiley Online Library and any embedding, framing or otherwise making available the article or pages thereof by third parties from platforms, services and websites other than Wiley Online Library must be prohibited.

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