Synthesis and electronic properties of A<sub>3</sub>B-thienyl porphyrins: experimental and computational investigations

Kumar, P. Ram; Britto, Neethinathan Johnee; Kathiravan, Arunkumar; Neels, Antonia; Jaccob, Madhavan; Mothi, Ebrahim M.

doi:10.1039/c8nj04289f

Cited by 23 publications

(23 citation statements)

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“…[a] Potential values are taken from differential pulse voltammograms. [b] E (LUMO)=−( E red +4.54) eV; E (HOMO)=−( E ox +4.54) eV . [c] E g opt =1240/ λ a.e .…”

Section: Resultsmentioning

confidence: 99%

“…[b] E(LUMO) = À(E red + 4.54) eV; E(HOMO) = À(E ox + 4.54) eV. [78] [c] E g opt = 1240/l a.e . [79] [d] Referencev alues.…”

Section: Photostabilitymentioning

confidence: 99%

“…[79] [d] Referencev alues. [78] Figure 7. Electrochemicalcharacteristics of different TATBPs, measured in CH 2 Cl 2 ,containing0 .1 m TBAPF 6 :a)cyclicvoltammogramo f2 at as can rate of 100 mVs À1 ;b)the influence of the electronic nature:normalized different pulse voltammogram of 2, 19,a nd 21 at as can rate of 10 mVs À1 ;c )influence of the positiona nd the amount of fluorine atoms withint he aryl moiety:n ormalized different pulse voltammogram of 7, 8,a nd 10 at as can rate of 10 mVs À1 .…”

Section: Photostabilitymentioning

confidence: 99%

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A Comprehensive Study on Tetraaryltetrabenzoporphyrins

Ruppel

Lungerich

Sturm

et al. 2020

Chemistry A European J

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Tetraaryltetrabenzoporphyrins (TATBPs) show, due to their optoelectronic properties, rising potential as dyes in various fields of physical and biomedical sciences. However, unlike in the case of porphyrins, the potential structural diversity of TATBPs has been explored only to little extent, owed mainly to synthetic hurdles. Herein, we prepared a comprehensive library of 30 TATBPs and investigated their fundamental properties. We elucidated structural properties by X‐ray crystallography and found explanations for physical properties such as solubility. Fundamental electronic aspects were studied by optical spectroscopy as well as by electrochemistry and brought in context to the stability of the molecules. Finally, we were able to develop a universal synthetic protocol, utilizing a readily established isoindole synthon, which gives TATBPs in high yields, regardless of the nature of the used arylaldehyde and without meticulous chromatographic purifications steps. This work serves as point of orientation for scientists, that aim to utilize these molecules in materials, nanotechnological, and biomedical applications.

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“…[a] Potential values are taken from differential pulse voltammograms. [b] E (LUMO)=−( E red +4.54) eV; E (HOMO)=−( E ox +4.54) eV . [c] E g opt =1240/ λ a.e .…”

Section: Resultsmentioning

confidence: 99%

“…[b] E(LUMO) = À(E red + 4.54) eV; E(HOMO) = À(E ox + 4.54) eV. [78] [c] E g opt = 1240/l a.e . [79] [d] Referencev alues.…”

Section: Photostabilitymentioning

confidence: 99%

Section: Photostabilitymentioning

confidence: 99%

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A Comprehensive Study on Tetraaryltetrabenzoporphyrins

Ruppel

Lungerich

Sturm

et al. 2020

Chemistry A European J

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“…All the freebase porphyrins produced four Q bands due to the split‐up of Q (0,0) and Q (1,0) bands that are caused by the symmetry break up by −NH protons, whereas the metalloporphyrins exhibit one or two Q bands in the low energy region. The thienyl groups of the porphyrins interact reasonably with the porphyrin core due to its small size that causes a reduction of the electronic transition energy resulting in redshifts of the absorption bands [6,10] …”

Section: Resultsmentioning

confidence: 99%

“…The mass spectral data of cationic porphyrins show peaks corresponding to their porphyrin triflate, and there is a good agreement with the observed and calculated values. The voltammograms of porphyrins P1‐P3 exhibited two successive one‐electron reductions at the conjugated macrocycle that leads to the formation of π‐anion radical and dianion whereas the dicationic porphyrins showed two porphyrin ring reduction peaks as well as two reduction peaks owing to their substituents [10] (Figure 4). The comparison of electrochemical redox potentials for porphyrins, P1‐P4 in DMF using 0.1 M TBAHFP at 25 °C is given at Table S2.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, TDDFT Calculations and Biological Evaluation of Dicationic Porphyrins as Groove Binders and Antimicrobial Agents

et al. 2021

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A2B2 porphyrin bearing 2/3‐thienyl and 2‐pyridyl moieties (P1a, P3a) and its dicationic derivatives (P2a, P4a) were synthesized in reasonably good yield. The corresponding Copper (II) (P1‐4 b) and Zinc (II) metallated (P1‐4 c) analogs were obtained by conventional methods. The synthesized compounds were characterized by various spectroscopic techniques, electrochemical studies and thermogravimetric analysis. The Copper (II) porphyrin, P1b is structurally characterized by single‐crystal X‐ray structure analysis. The ground state electronic structure and geometry optimizations are carried out by DFT calculations. The computed TD‐DFT results validate the observed optical bands and spectral features. DNA interaction studies of trans‐dicationic porphyrins were performed using spectroscopic titrations, docking studies, and gel electrophoresis experiments. All porphyrins interact with the calf thymus DNA by outside groove binding mode with self‐stacking, and the highest intrinsic binding constant of 1.29 ± 0.14×106 M‐1 is observed for P4a. Molecular docking studies reveal that the binding energy of porphyrins with DNA is around −10 kcal/mol. The antimicrobial properties of the dicationic derivatives (P2,4 a, b, c) were investigated against E. Coli and S. aureus under light and dark conditions, and the growth inhibitory effect is found to be negligible when unilluminated.

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Porphyrinbasiertes organisches Netzwerk bestehend aus nachhaltigen Kohlenstoffpunkten für die Photopolymerisation

Luo¹,

Wan²,

et al. 2022

Angewandte Chemie

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Nachhaltige Kohlenstoffpunkte (CDs) auf der Basis von Furfural (F-CD) führten nach Durchführung der Alder-Longo-Reaktion zu einem lichtempfindlichen Material. Die gebildete Porphyrineinheit verbindet die F-CDs zu einem kovalenten organischen Netzwerk. Dieses heterogene Material (P-CD) wurde mit XPS charakterisiert, was auf den Einbau der jeweiligen C-, N-und O-Einheiten hinweist. Zeitaufgelöste Fluoreszenz einschließlich der Globalanalyse zeigte einen Beitrag von drei verknüpften Komponenten zur Beschreibung der Gesamtdynamik des angeregten Zustands. Die elektrochemischen und photonischen Eigenschaften dieses heterogenen Materials ermöglichten eine Photopolymerisation mittels photo-ATRP, bei der entweder CuBr 2 /TPMA, FeBr 3 /Br À oder ein metallfreier Ansatz die kontrollierte Polymerisation aktivierte. Kettenverlängerungsexperimente funktionierten in allen drei Fällen und zeigten die Aktivität der Endgruppe für die Aktivierung der kontrollierten Blockcopolymerisation unter Verwendung von MMA und Styren als Monomere. Die traditionelle radikalische Polymerisation unter Einsatz eines Diaryliodoniumsalzes als Coinitiator scheiterte.

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Synthesis and electronic properties of A₃B-thienyl porphyrins: experimental and computational investigations

Abstract: A facile synthesis of meso-thienyl porphyrins containing a phenyl substituent allows fine tuning of the frontier orbitals to suit applications in DSSC and photomedicine.

Cited by 23 publications

References 50 publications

A Comprehensive Study on Tetraaryltetrabenzoporphyrins

A Comprehensive Study on Tetraaryltetrabenzoporphyrins

Synthesis, TDDFT Calculations and Biological Evaluation of Dicationic Porphyrins as Groove Binders and Antimicrobial Agents

Porphyrinbasiertes organisches Netzwerk bestehend aus nachhaltigen Kohlenstoffpunkten für die Photopolymerisation

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Synthesis and electronic properties of A3B-thienyl porphyrins: experimental and computational investigations

Abstract: A facile synthesis of meso-thienyl porphyrins containing a phenyl substituent allows fine tuning of the frontier orbitals to suit applications in DSSC and photomedicine.

Cited by 23 publications

References 50 publications

A Comprehensive Study on Tetraaryltetrabenzoporphyrins

A Comprehensive Study on Tetraaryltetrabenzoporphyrins

Synthesis, TDDFT Calculations and Biological Evaluation of Dicationic Porphyrins as Groove Binders and Antimicrobial Agents

Porphyrinbasiertes organisches Netzwerk bestehend aus nachhaltigen Kohlenstoffpunkten für die Photopolymerisation

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Synthesis and electronic properties of A₃B-thienyl porphyrins: experimental and computational investigations