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Revisiting fluorenone photophysics via dipolar fluorenone derivatives.

Leandro A Estrada¹, James E Yarnell, Douglas C Neckers

¹Center for Photochemical Sciences at Bowling Green State University, Bowling Green, Ohio 43403, United States.

The Journal of Physical Chemistry. A

|May 20, 2011

Summary

Nonradiative decay in fluorenone derivatives (FODs) was studied. Carbazole-containing FODs primarily use charge separation/recombination, while 3,6-disubstituted variants show intersystem crossing (ISC).

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Area of Science:

Photochemistry
Organic Chemistry
Computational Chemistry

Background:

Fluorenone derivatives (FODs) are important organic molecules.
Understanding nonradiative decay pathways is crucial for designing new materials.

Purpose of the Study:

To investigate the nonradiative decay mechanisms of four dipolar fluorenone derivatives (FODs).
To elucidate the role of substituents and solvent polarity on excited state deactivation pathways.

Main Methods:

Steady-state and time-resolved UV-vis absorption and fluorescence spectroscopy.
Cyclic voltammetry.
Density Functional Theory (DFT) calculations for frontier orbital analysis.

Main Results:

The first singlet excited state was identified as π-π* across all FODs and solvent polarities.
Charge separation/recombination dominated excited state deactivation in carbazole-containing FODs.
Intersystem crossing (ISC) was the exclusive deactivation pathway in 3,6-disubstituted FODs, competing with charge transfer (CT) in CPAFO36.

Conclusions:

Nonradiative decay in FODs is highly dependent on molecular structure and substitution patterns.
ISC is a significant deactivation pathway for 3,6-disubstituted FODs.
The findings provide insights into controlling photophysical properties of fluorenone derivatives.