Photophysical and electrochemical properties of meso-tetrathien-2′-yl porphyrins compared to meso-tetraphenylporphyrin

Jessica S. O'Neill; Nicola M. Boyle; Thayse Marques Passos; Katharina Heintz; Wesley R. Browne; Brid Quilty; Mary T. Pryce

doi:10.1016/j.jphotochem.2023.114573

Photophysical and electrochemical properties of meso-tetrathien-2′-yl porphyrins compared to meso-tetraphenylporphyrin

Jessica S. O'Neill, Nicola M. Boyle, Thayse Marques Passos, Katharina Heintz, Wesley R. Browne^*, Brid Quilty^*, Mary T. Pryce^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › Academic › peer-review

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Abstract

A series of novel tetra-meso-thien-2-yl porphyrins were synthesised, and the effect of the variation in the thienyl group on the photophysical properties were studied. Ground and excited state UV–vis absorption, steady-state and time-resolved emission, resonance Raman spectroscopy, and cyclic voltammetry, were used to establish the extent of electronic communication between the central Zn(II) porphyrin ring and the various meso-substituent groups. The properties of these novel thienyl porphyrins were compared to zinc tetraphenylporphyrin (ZnTPP), to elucidate the effect of the position and number of thienyl rings. The photochemically-driven antimicrobial activity of zinc(II)-5,10,15,20-tetra(thien-2′-yl)porphyrin (ZnThPP) as a coating, was established against both Gram-positive and Gram-negative bacteria, and compared to ZnTPP. Visible irradiation of the porphyrins results in a significant antimicrobial response.

Original language	English
Article number	114573
Number of pages	8
Journal	Journal of Photochemistry and Photobiology A: Chemistry
Volume	438
DOIs	https://doi.org/10.1016/j.jphotochem.2023.114573
Publication status	Published - 1-Apr-2023

Keywords

Porphyrin
Thiophene
Photophysical
Electrochemistry
Raman
Singlet oxygen
Antimicrobial

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@article{0e65753a59b64bafa30983d81773a64a,

title = "Photophysical and electrochemical properties of meso-tetrathien-2′-yl porphyrins compared to meso-tetraphenylporphyrin",

abstract = "A series of novel tetra-meso-thien-2-yl porphyrins were synthesised, and the effect of the variation in the thienyl group on the photophysical properties were studied. Ground and excited state UV–vis absorption, steady-state and time-resolved emission, resonance Raman spectroscopy, and cyclic voltammetry, were used to establish the extent of electronic communication between the central Zn(II) porphyrin ring and the various meso-substituent groups. The properties of these novel thienyl porphyrins were compared to zinc tetraphenylporphyrin (ZnTPP), to elucidate the effect of the position and number of thienyl rings. The photochemically-driven antimicrobial activity of zinc(II)-5,10,15,20-tetra(thien-2′-yl)porphyrin (ZnThPP) as a coating, was established against both Gram-positive and Gram-negative bacteria, and compared to ZnTPP. Visible irradiation of the porphyrins results in a significant antimicrobial response.",

keywords = "Porphyrin, Thiophene, Photophysical, Electrochemistry, Raman, Singlet oxygen, Antimicrobial",

author = "O'Neill, \{Jessica S.\} and Boyle, \{Nicola M.\} and \{Marques Passos\}, Thayse and Katharina Heintz and Browne, \{Wesley R.\} and Brid Quilty and Pryce, \{Mary T.\}",

note = "Funding Information: The authors gratefully acknowledges financial funding provided by the Sustainable Energy Authority of Ireland (under the SEAI National Energy Research, Development \& Demonstration Funding Programme 2018, Grant number 18/RDD/282), Dublin City University for a scholarship (NMB) and from SFI (19/FFP/6882). Publisher Copyright: {\textcopyright} 2023 The Author(s)",

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doi = "10.1016/j.jphotochem.2023.114573",

language = "English",

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T1 - Photophysical and electrochemical properties of meso-tetrathien-2′-yl porphyrins compared to meso-tetraphenylporphyrin

AU - O'Neill, Jessica S.

AU - Boyle, Nicola M.

AU - Marques Passos, Thayse

AU - Heintz, Katharina

AU - Browne, Wesley R.

AU - Quilty, Brid

AU - Pryce, Mary T.

N1 - Funding Information: The authors gratefully acknowledges financial funding provided by the Sustainable Energy Authority of Ireland (under the SEAI National Energy Research, Development & Demonstration Funding Programme 2018, Grant number 18/RDD/282), Dublin City University for a scholarship (NMB) and from SFI (19/FFP/6882). Publisher Copyright: © 2023 The Author(s)

PY - 2023/4/1

Y1 - 2023/4/1

N2 - A series of novel tetra-meso-thien-2-yl porphyrins were synthesised, and the effect of the variation in the thienyl group on the photophysical properties were studied. Ground and excited state UV–vis absorption, steady-state and time-resolved emission, resonance Raman spectroscopy, and cyclic voltammetry, were used to establish the extent of electronic communication between the central Zn(II) porphyrin ring and the various meso-substituent groups. The properties of these novel thienyl porphyrins were compared to zinc tetraphenylporphyrin (ZnTPP), to elucidate the effect of the position and number of thienyl rings. The photochemically-driven antimicrobial activity of zinc(II)-5,10,15,20-tetra(thien-2′-yl)porphyrin (ZnThPP) as a coating, was established against both Gram-positive and Gram-negative bacteria, and compared to ZnTPP. Visible irradiation of the porphyrins results in a significant antimicrobial response.

AB - A series of novel tetra-meso-thien-2-yl porphyrins were synthesised, and the effect of the variation in the thienyl group on the photophysical properties were studied. Ground and excited state UV–vis absorption, steady-state and time-resolved emission, resonance Raman spectroscopy, and cyclic voltammetry, were used to establish the extent of electronic communication between the central Zn(II) porphyrin ring and the various meso-substituent groups. The properties of these novel thienyl porphyrins were compared to zinc tetraphenylporphyrin (ZnTPP), to elucidate the effect of the position and number of thienyl rings. The photochemically-driven antimicrobial activity of zinc(II)-5,10,15,20-tetra(thien-2′-yl)porphyrin (ZnThPP) as a coating, was established against both Gram-positive and Gram-negative bacteria, and compared to ZnTPP. Visible irradiation of the porphyrins results in a significant antimicrobial response.

KW - Porphyrin

KW - Thiophene

KW - Photophysical

KW - Electrochemistry

KW - Raman

KW - Singlet oxygen

KW - Antimicrobial

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U2 - 10.1016/j.jphotochem.2023.114573

DO - 10.1016/j.jphotochem.2023.114573

M3 - Article

AN - SCOPUS:85147282857

SN - 1010-6030

VL - 438

JO - Journal of Photochemistry and Photobiology A: Chemistry

JF - Journal of Photochemistry and Photobiology A: Chemistry

M1 - 114573

ER -

Photophysical and electrochemical properties of meso-tetrathien-2′-yl porphyrins compared to meso-tetraphenylporphyrin

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