2015
DOI: 10.1021/acs.jpcb.5b08025
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Relaxation Process of Photoexcited meso-Naphthylporphyrins while Interacting with DNA and Singlet Oxygen Generation

Abstract: Electron donor-connecting cationic porphyrins meso-(1-naphthyl)-tris(N-methyl-p-pyridinio)porphyrin (1-NapTMPyP) and meso-(2-naphthyl)-tris(N-methyl-p-pyridinio)porphyrin (2-NapTMPyP) were designed and synthesized. DFT calculations speculate that the photoexcited states of 1- and 2-NapTMPyPs can be deactivated via intramolecular electron transfer from the naphthyl moiety to the porphyrin moiety. However, the quenching effect through the intramolecular electron transfer is insufficient, possibly due to the orth… Show more

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Cited by 17 publications
(16 citation statements)
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“…Copper ion induces Cu(I)-OOH formation from H 2 O 2 , Figure 19. The examples of DNA-targeting porphyrins: Ant-P [81], Pyr-P [130], Phen-P [131], and Nap-Ps [132].…”
Section: Discussionmentioning
confidence: 99%
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“…Copper ion induces Cu(I)-OOH formation from H 2 O 2 , Figure 19. The examples of DNA-targeting porphyrins: Ant-P [81], Pyr-P [130], Phen-P [131], and Nap-Ps [132].…”
Section: Discussionmentioning
confidence: 99%
“…DNA-targeting control of photosensitized 1 O 2 generation has been also reported [127,128]. For example, electron donor-connecting porphyrins have been studied (Figure 19) [81,[130][131][132]. These compounds can be photoexcited by visible light irradiation, and their S 1 states are effectively quenched through intramolecular electron transfer.…”
Section: Control Of Singlet Oxygen Productionmentioning
confidence: 93%
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“…On the other hand, in the case of phenanthrylporphyrin, the S 1 state of this porphyrin could not be deactivated through intramolecular electron transfer because the electron-donating property of the phenanthryl moiety was insufficient [56]. To investigate the factors governing the activity control of the electron donor-connecting porphyrins, two types of electron donor-connecting porphyrins, meso-(1-naphthyl)-tris(N-methyl-p-pyridinio)porphyrin (1-NapTPP) and meso-(2-naphthyl)-tris(N-methyl-p-pyridinio)porphyrin (2-NapTPP) (Figure 11), were designed and synthesized [57].…”
Section: Factors Governing the Activity Control Of The Photochemical mentioning
confidence: 99%
“…These naphthylporphyrins, 1-NapTPP and 2-NapTPP, spontaneously bind to doublestranded DNA [57]. The electrostatic force between cationic porphyrins and the anionic DNA strand, as well as the hydrophobic interaction, can be speculated as the driving force of the binding interaction.…”
Section: Factors Governing the Activity Control Of The Photochemical mentioning
confidence: 99%