Enhancing two-photon uncaging sensitivity in symmetrical dimeric conjugated coumarin cages: Role of the coupling core

Victor Dubois, Maxime Klausen, Frédéric Castet, Jean Baptiste Verlhac*, Mireille Blanchard-Desce

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

Abstract / Description of output

A series of symmetrical conjugated dimeric coumarinyl cages has been synthesized by grafting 7-diethlyaminocoumarin (DEAC) cages via π-linkers onto different aromatic cores displaying various electronic character (electron-withdrawing: benzobisthiazole BBTz, electron-donating: carbazole or ambivalent: fluorenyl). Due to their symmetrical design, all conjugated dimeric derivatives showed enhanced two-photon absorption at 730 nm, the electron-withdrawing core leading to the highest response (over 3000 GM). All dimeric derivatives retained the uncaging ability of the DEAC cage, with a strong influence of the nature of the core on the uncaging quantum yield. While the fluorenyl core led to an uncaging quantum yield similar to DEAC, the BBTz core led to a twice larger uncaging quantum yield and the carbazole core to even larger uncaging quantum yield (60 %). As a result, both electron-donating and electron-withdrawing cores lead to symmetrical dimeric DEAC derivatives showing unprecedented two-photon uncaging photo-sensitivity (up to 550 GM).

Original languageEnglish
Article number114544
JournalJournal of Photochemistry and Photobiology A: Chemistry
Volume438
Early online date7 Jan 2023
DOIs
Publication statusE-pub ahead of print - 7 Jan 2023

Keywords / Materials (for Non-textual outputs)

  • Coumarins
  • Photorelease
  • Photosensitive Protecting Groups
  • Two-Photon Absorption
  • Uncaging

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