Tuning the Absorption, Fluorescence, Intramolecular Charge Transfer, and Intersystem Crossing in Spiro (fluorene) acridinone

Abstract: In this work, we prepared a series of electron donor‐acceptor systems based on spiro[fluorene‐9,7’‐dibenzo[c,h]acridine]‐5’‐one (SFDBAO). Our SFDBAOs consist of orthogonally positioned fluorenes and aromatic ketones. By fine‐tuning the substitution of electron‐donating pyrenes, the complex interplay among different excited‐state decay channels and the overall impact of solvents on these decay channels were uncovered. Placing pyrene, for example, at the aromatic ketones resulted in a profound solvatochromism in the form of a bright charge‐transfer (CT) emission spanning from yellow to red‐NIR. In contrast, a dark non‐emissive CT was noted upon pyrene substitution at the fluorenes. In apolar solvents, efficient triplet‐excited state generation was observed for all SFDBAOs. Either charge transfer was concluded to mediate the intersystem crossing (ISC) in the case of pyrene substitution or the El‐Sayed rule was applicable when lacking pyrene substitution as in the case of SFABAO. In polar solvents, charge separation is the sole decay upon pyrene substitution. Moreover, competition between ISC and CT lowered the triplet‐excited state generation in SFDBAO.

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

Bibliographic citation
Tuning the Absorption, Fluorescence, Intramolecular Charge Transfer, and Intersystem Crossing in Spiro (fluorene) acridinone ; day:20 ; month:02 ; year:2024 ; extent:12
Angewandte Chemie / International edition. International edition ; (20.02.2024) (gesamt 12)

Creator
Bo, Yifan
Zhang, He
Li, Yue
Reva, Yana
Xie, Linghai
Guldi, Dirk M.

DOI
10.1002/anie.202313936
URN
urn:nbn:de:101:1-2024022115090019092585
Rights
Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.
Last update
14.08.20252025, 10:51 AM CEST

Data provider

This object is provided by:
Deutsche Nationalbibliothek. If you have any questions about the object, please contact the data provider.

Associated

  • Bo, Yifan
  • Zhang, He
  • Li, Yue
  • Reva, Yana
  • Xie, Linghai
  • Guldi, Dirk M.

Other Objects (12)