Anion-Mediated Synthesis of Diethynyl-Substituted Doubly N-Confused Dioxohexaphyrin Dyes That Exhibit Enhanced Photoacoustic Signals in the NIR-II Region
We herein report the anion-mediated synthesis of diethynyl-substituted doubly N-confused dioxohexaphyrins with hydrogen sulfate anions in an acid condensation of the tripyrrane and silyl-protected propiolaldehyde and subsequent oxidation in a one-pot fashion. Further, functionalization through <i>in situ</i> silyl deprotection and Sonogashira cross-coupling reaction yielded the anisotropically π-extended derivative along a longer molecular axis. The modified hexaphyrin dye exhibited an intense S<sub>0</sub> → S<sub>1</sub> transition at around 1100 nm in the near-infrared-II region and enhanced photoacoustic signal intensity suitable for high-resolution imaging applications.
Authors
- Shigeki Mori (ORCID: https://orcid.org/0000-0001-6731-2357)
- Yuma Nakamura
- Hiroyuki Furuta (ORCID: https://orcid.org/0000-0002-3881-8807)
- Hiroto Kai
- Yusuke Notsuka (ORCID: https://orcid.org/0000-0002-3733-0121)
- Yoshihisa Yamaoka (ORCID: https://orcid.org/0000-0001-6395-7721)
- Masatoshi Ishida
- Daisuke Kawaguchi (ORCID: https://orcid.org/0000-0001-8930-039X)
- Koreyuki Kai
- Shashikant V. Bhandari (ORCID: https://orcid.org/0000-0001-9661-9921)
- Tatsuki Abe (ORCID: https://orcid.org/0000-0001-9923-8032)
Institutions
- Shanghai University (CN)
- Kyushu University (JP)
- Saga University (JP)
- Komatsu University (JP)
- Fusion (United States) (US)
- Fusion Academy (US)
- Sustainable Energy Systems (United Kingdom) (GB)
- Ehime University (JP)
- Tokyo Metropolitan University (JP)
- Graduate School USA (US)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-06-19
- DOI
- https://doi.org/10.1021/acs.orglett.5c02171
- Citations
- 3
- Primary Topic
- Nanoplatforms for cancer theranostics
- Type
- article
- Field-Weighted Citation Impact
- 2.02
Funders
- Asahi Glass Foundation
- Iwatani Naoji Foundation
- Shorai Foundation for Science and Technology
- Izumi Science and Technology Foundation
- Japan Society for the Promotion of Science