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Article

Linear and Nonlinear Optical Properties of Quadrupolar Bithiophenes and Cyclopentadithiophenes as Fluorescent Oxygen Photosensitizers

by
Nicolas Richy
1,
Safa Gam
1,2,3,
Sabri Messaoudi
2,3,4,
Amédée Triadon
1,5,
Olivier Mongin
1,
Mireille Blanchard-Desce
6,
Camille Latouche
7,
Mark G. Humphrey
5,
Abdou Boucekkine
1,*,
Jean-François Halet
8,* and
Frédéric Paul
1,*
1
Univ Rennes, CNRS, Institut des Sciences Chimiques de Rennes (ISCR)—UMR 6226, F-35000 Rennes, France
2
Faculty of Sciences of Bizerte FSB, University of Carthage, Jarzouna 7021, Tunisia
3
Laboratory of Materials, Molecules and Applications, IPEST, University of Carthage, SidiBou Said Road, B.P. 51, La Marsa 2070, Tunisia
4
Department of Chemistry, College of Science, Qassim University, Buraidah 51452, Saudi Arabia
5
Research School of Chemistry, Australian National University, Canberra, ACT 2601, Australia
6
Univ. Bordeaux, CNRS, Bordeaux INP, ISM (UMR5255), Bat A12, 351 Cours de la Libération, F-33405 Talence, France
7
Nantes Université, CNRS, IMN (Institut des Matériaux de Nantes Jean Rouxel), F-44000 Nantes, France
8
CNRS—Saint-Gobain—NIMS, IRL 3629, Laboratory for Innovative Key Materials and Structures (LINK), National Institute for Materials Science (NIMS), Tsukuba 305-0044, Japan
*
Authors to whom correspondence should be addressed.
Photochem 2023, 3(1), 127-154; https://doi.org/10.3390/photochem3010009
Submission received: 10 January 2023 / Revised: 7 February 2023 / Accepted: 8 February 2023 / Published: 20 February 2023
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Abstract

The linear and nonlinear optical properties of two quadrupolar bithiophenes and two quadrupolar cyclopentadithiophenes have been investigated. At the 5,5′ positions of the central bi/dithiophene units, the molecules possess 1,4-phenylalkynyl groups that bear either electron-donating (NPh2) or electron-withdrawing (SO2CF3) groups. The optical properties were experimentally studied and modelled via quantum chemistry computations of key configurations and conformations. All the compounds show good light harvesting efficiency due to their strong absorption in the visible range. These fluorescent compounds are also good two-photon absorbers in the NIR range that can photosensitize oxygen in toluene. DFT calculations reveal that the mixtures of conformers in a solution show similar linear optical properties. TD-DFT calculations reproduce the experimental spectroscopic data fairly well, including vibronic couplings in the fluorescence spectra. The lowest excited state for two-photon absorption corresponds to the S2 state. The roles of the SO2CF3 and NPh2 terminal groups on the nonlinear response were analyzed for possible bio-oriented applications, with the cyclopentadithiophenes showing the most promising figures of merit.
Keywords: bithiophenes; DFT calculations; fluorescence; oxygen photosensitization; two-photon absorption bithiophenes; DFT calculations; fluorescence; oxygen photosensitization; two-photon absorption

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MDPI and ACS Style

Richy, N.; Gam, S.; Messaoudi, S.; Triadon, A.; Mongin, O.; Blanchard-Desce, M.; Latouche, C.; Humphrey, M.G.; Boucekkine, A.; Halet, J.-F.; et al. Linear and Nonlinear Optical Properties of Quadrupolar Bithiophenes and Cyclopentadithiophenes as Fluorescent Oxygen Photosensitizers. Photochem 2023, 3, 127-154. https://doi.org/10.3390/photochem3010009

AMA Style

Richy N, Gam S, Messaoudi S, Triadon A, Mongin O, Blanchard-Desce M, Latouche C, Humphrey MG, Boucekkine A, Halet J-F, et al. Linear and Nonlinear Optical Properties of Quadrupolar Bithiophenes and Cyclopentadithiophenes as Fluorescent Oxygen Photosensitizers. Photochem. 2023; 3(1):127-154. https://doi.org/10.3390/photochem3010009

Chicago/Turabian Style

Richy, Nicolas, Safa Gam, Sabri Messaoudi, Amédée Triadon, Olivier Mongin, Mireille Blanchard-Desce, Camille Latouche, Mark G. Humphrey, Abdou Boucekkine, Jean-François Halet, and et al. 2023. "Linear and Nonlinear Optical Properties of Quadrupolar Bithiophenes and Cyclopentadithiophenes as Fluorescent Oxygen Photosensitizers" Photochem 3, no. 1: 127-154. https://doi.org/10.3390/photochem3010009

APA Style

Richy, N., Gam, S., Messaoudi, S., Triadon, A., Mongin, O., Blanchard-Desce, M., Latouche, C., Humphrey, M. G., Boucekkine, A., Halet, J.-F., & Paul, F. (2023). Linear and Nonlinear Optical Properties of Quadrupolar Bithiophenes and Cyclopentadithiophenes as Fluorescent Oxygen Photosensitizers. Photochem, 3(1), 127-154. https://doi.org/10.3390/photochem3010009

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