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Naphthodithiophene‐Fused Porphyrins: Synthesis, Characterization, and Impact of Extended Conjugation on Aromaticity
Abstract
Abstract The fusion of tetrapyrroles with aromatic heterocycles constitutes a useful tool for manipulating their opto‐electronic properties. In this work, the synthesis of naphthodithiophene‐fused porphyrins was achieved through a Heck reaction‐based cascade of steps followed by the Scholl reaction. The naphthodithiophene‐fused porphyrins display a unique set of optical and electronic properties. Fusion of the naphtho[2,1‐b:3,4‐b’]dithiophene to porphyrin ( F2VTP ) leads to a ~20% increase in the fluorescence lifetime, which is accompanied, unexpectedly, by a more than two‐fold drop in the emission quantum yield ( ϕ =0.018). In contrast, fusion of the isomeric naphtho[1,2‐b:4,3‐b’]dithiophene to porphyrin ( F3VPT) results in a ~1.5‐fold increase in the fluorescence quantum yield ( ϕ =0.13) with a concomitant ~30 % increase in the fluorescence lifetime. This behavior suggests that fusion of the porphyrin with the naphthodithiopheno‐system mainly affects the radiative rate constant in the Q‐state deactivation pathway, where the effects of the isomeric naphtho[2,1‐b:3,4‐b’]dithiophene‐ versus naphtho[1,2‐b:4,3‐b’]dithiophene‐fusion are essentially the opposite. Interestingly, nucleus‐independent chemical shifts analysis revealed a considerable difference between the aromaticities of these two isomeric systems. Our results demonstrate that subtle structural differences in the fused components of the porphyrin can be reflected in rather significant differences between the photophysical properties of the resultingmore »
- Authors:
-
[1]
- Department of Chemistry University of North Texas Denton TX 76203 USA
- Department of Biochemistry and Biophysics Perelman School of Medicine and Department of Chemistry School of Arts and Sciences University of Pennsylvania Philadelphia PA 19104 USA
- Publication Date:
- Sponsoring Org.:
- USDOE
- OSTI Identifier:
- 1999286
- Grant/Contract Number:
- SC0016766)
- Resource Type:
- Publisher's Accepted Manuscript
- Journal Name:
- Chemistry - A European Journal
- Additional Journal Information:
- Journal Name: Chemistry - A European Journal; Journal ID: ISSN 0947-6539
- Publisher:
- Wiley Blackwell (John Wiley & Sons)
- Country of Publication:
- Germany
- Language:
- English
Citation Formats
Cooper, Courtney, Paul, Ros, Alsaleh, Ajyal, Washburn, Spenser, Rackers, William, Kumar, Siddhartha, Nesterov, Vladimir N., D'Souza, Francis, Vinogradov, Sergei A., and Wang, Hong. Naphthodithiophene‐Fused Porphyrins: Synthesis, Characterization, and Impact of Extended Conjugation on Aromaticity. Germany: N. p., 2023.
Web. doi:10.1002/chem.202302013.
Cooper, Courtney, Paul, Ros, Alsaleh, Ajyal, Washburn, Spenser, Rackers, William, Kumar, Siddhartha, Nesterov, Vladimir N., D'Souza, Francis, Vinogradov, Sergei A., & Wang, Hong. Naphthodithiophene‐Fused Porphyrins: Synthesis, Characterization, and Impact of Extended Conjugation on Aromaticity. Germany. https://doi.org/10.1002/chem.202302013
Cooper, Courtney, Paul, Ros, Alsaleh, Ajyal, Washburn, Spenser, Rackers, William, Kumar, Siddhartha, Nesterov, Vladimir N., D'Souza, Francis, Vinogradov, Sergei A., and Wang, Hong. Mon .
"Naphthodithiophene‐Fused Porphyrins: Synthesis, Characterization, and Impact of Extended Conjugation on Aromaticity". Germany. https://doi.org/10.1002/chem.202302013.
@article{osti_1999286,
title = {Naphthodithiophene‐Fused Porphyrins: Synthesis, Characterization, and Impact of Extended Conjugation on Aromaticity},
author = {Cooper, Courtney and Paul, Ros and Alsaleh, Ajyal and Washburn, Spenser and Rackers, William and Kumar, Siddhartha and Nesterov, Vladimir N. and D'Souza, Francis and Vinogradov, Sergei A. and Wang, Hong},
abstractNote = {Abstract The fusion of tetrapyrroles with aromatic heterocycles constitutes a useful tool for manipulating their opto‐electronic properties. In this work, the synthesis of naphthodithiophene‐fused porphyrins was achieved through a Heck reaction‐based cascade of steps followed by the Scholl reaction. The naphthodithiophene‐fused porphyrins display a unique set of optical and electronic properties. Fusion of the naphtho[2,1‐b:3,4‐b’]dithiophene to porphyrin ( F2VTP ) leads to a ~20% increase in the fluorescence lifetime, which is accompanied, unexpectedly, by a more than two‐fold drop in the emission quantum yield ( ϕ =0.018). In contrast, fusion of the isomeric naphtho[1,2‐b:4,3‐b’]dithiophene to porphyrin ( F3VPT) results in a ~1.5‐fold increase in the fluorescence quantum yield ( ϕ =0.13) with a concomitant ~30 % increase in the fluorescence lifetime. This behavior suggests that fusion of the porphyrin with the naphthodithiopheno‐system mainly affects the radiative rate constant in the Q‐state deactivation pathway, where the effects of the isomeric naphtho[2,1‐b:3,4‐b’]dithiophene‐ versus naphtho[1,2‐b:4,3‐b’]dithiophene‐fusion are essentially the opposite. Interestingly, nucleus‐independent chemical shifts analysis revealed a considerable difference between the aromaticities of these two isomeric systems. Our results demonstrate that subtle structural differences in the fused components of the porphyrin can be reflected in rather significant differences between the photophysical properties of the resulting systems.},
doi = {10.1002/chem.202302013},
journal = {Chemistry - A European Journal},
number = ,
volume = ,
place = {Germany},
year = {Mon Sep 11 00:00:00 EDT 2023},
month = {Mon Sep 11 00:00:00 EDT 2023}
}
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- Accounts of Chemical Research, Vol. 52, Issue 9