Tuning the Electronic Properties of Porphyrin Dyes: Effects of <i>meso</i> Substitution on Their Optical and Electrochemical Behaviour

Ragoussi, Maria‐Eleni; Torre, Gema de la; Torres, Tomás

doi:10.1002/ejoc.201300124

Cited by 33 publications

(24 citation statements)

References 28 publications

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“…The synthesis of dyes 1a,b was performed starting from trimethylsilylporphyrin 2 (Scheme 1) [10,21]. Firstly, the trimethylsilyl group was quantitatively removed by reaction with TBAF and this was followed by copper-free Pd-catalysed Sonogashira coupling [22] with 2-iodothiophene derivatives 3aeb [23,24] Under these conditions, the reaction proceeded smoothly to afford aldehydes 4a,b in 83% and 80% yield, respectively.…”

Section: Resultsmentioning

confidence: 99%

“…The first oxidation potential (1a: E 1 ox ¼ 0.29 V; 1b: 0.26 V) corresponds to the formation of the porphyrin radical cation and the second is due to the oxidation of the triphenylamino substituents (E 1 ox z 0.5 V) in both dyes [10,21]. The reduction processes occur throughout the whole conjugated system but in dye 1b the second reduction potential observed is due to the reduction of the porphyrin macrocycle (see electro-chemical studies).…”

Section: Theoretical Calculationsmentioning

confidence: 99%

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Charge recombination losses in thiophene-substituted porphyrin dye-sensitized solar cells

et al. 2016

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a b s t r a c tTwo new porphyrins that incorporate thiophene substituents as spacers between the conjugated porphyrin core and the anchoring cyanoacrylate group have been synthesised. The two dyes differ in the number of thiophene bridges; porphyrin 1a has only one thiophene group and porphyrin 1b has two thiophene rings connected by a double bond. The measured light-toenergy conversion efficiencies in 1a and 1b were assessed using two different electrolytes, LP1 and LP2, which differ in the presence of tert-butyl pyridine in LP1. An efficiency of 6% under standard measurement conditions has been achieved for 1a þ LP1. However, for porphyrin 1b the use of electrolyte LP1 led to lower efficiencies and a value of approximately 4% was obtained. The differences between the two types of solar cells and the electrolytes have been studied in-depth using photoinduced time-resolved techniques such as CE (Charge Extrac-tion) and TPV (Transient PhotoVoltage).

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Section: Resultsmentioning

confidence: 99%

Section: Theoretical Calculationsmentioning

confidence: 99%

Charge recombination losses in thiophene-substituted porphyrin dye-sensitized solar cells

et al. 2016

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“…Here, we present a quantitative elastic properties and structure correlation study of a series of ionically self-assembled (ISA) [17][18][19][20] crystalline p-conjugated solids fabricated from oppositely charged porphyrin tectons (binary porphyrins, BP). These materials are known to serve as active components in many optoelectronic devices such as solar cells [21][22][23][24], photovoltaics [1,17,25], and photosensors [26][27][28][29][30]. Until recently, reports of crystal structures of BPs were rare because synthesized crystals were not suitable for single crystal X-ray diffraction (XRD) [31][32][33][34].…”

Section: Introductionmentioning

confidence: 99%

Mechanical behavior of crystalline ionic porphyrins

Adinehnia

Eskelsen

Hipps

et al. 2019

J. Porphyrins Phthalocyanines

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Mechanical properties of six different binary ionic porphyrin crystals with variable morphologies were measured and correlated with their structural properties. These solids were formed from stoichiometric combinations of negatively charged tectons, meso-tetra(4-sulfonatophenyl)porphyrin (TSPP), Cu(II) meso-tetra(4-sulfonatophenyl)porphyrin (CuTSPP), Ni(II) meso-tetra (4-sulfonatophenyl)porphyrin (NiTSPP), and four different cationic tectons, namely, meso-tetra (4-pyridyl)porphyrin (TPyP), tetra([Formula: see text]-methyl-4-pyridyl)porphyrin (TMPyP), Cu(II) meso-tetra([Formula: see text]-methyl-4-pyridyl)porphyrin (CuTMPyP), Ni(II) meso-tetra([Formula: see text]-methyl-4-pyridyl)porphyrin (NiTMPyP), and tetra(4-aminophenyl)porphyrin (TAPP). Crystal structures were determined from single crystal and powder X-ray diffraction patterns. Scanning electron and atomic force microscopes (SEM and AFM) provided topographical information. The common arrangement of the porphyrin tectons within the crystals is consistent with alternating face-to-face molecular arrangement forming coherent columns along the fast-growing long axis which are held together by electrostatic and [Formula: see text]–[Formula: see text] interactions as well as hydrogen bonding. In acquiring the indentation data of the porphyrin crystals using AFM, stress was applied perpendicular to the direction where ionic and [Formula: see text]–[Formula: see text] bonds dominate the packing. At indent loads [Formula: see text]50 nN/nm2, all the porphyrin structures deformed elastically. Young’s modulus ([Formula: see text] values for the different crystals range from 6 to 28 GPa. In a broader perspective, this study highlights the extraordinary mechanical behavior of porphyrin assemblies formed by ionic self-assembly. Judicious selection of charged porphyrin synthons can yield crystalline materials with mechanical properties that combine the elastic characteristics of ‘soft’ polymers with the stiffness of composite materials. Such high-performance materials are excellent candidates for deformable optoelectronic devices.

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“…РОССИЙСКИЕ НАНОТЕХНОЛОГИИ том 14 № 7-8 2019 в качестве катализаторов [11,12], химических сенсоров [13], переносчиков кислорода [14], систем искусственного фотосинтеза [15]. При этом наиболее массовым использованием порфиринов остается производство красителей [16]. Получение супрамолекулярных комплексов, в том числе полимерных модификаций биологически активных соединений ряда порфиринов, является активно развивающимся научным направлением [17].…”

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Сравнительный Структурно-Динамический Анализ Ультратонких Волокон Поли-(3-Гидроксибутирата), Модифицированного Комплексами Тетрафенилпорфирина С Металлами

Карпова¹,

Olkhov²,

Чвалун³

et al. 2020

Rossijskie nanotehnologii

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Проведены комплексные исследования, сочетающие рентгеноструктурный анализ, термофизические, динамические измерения зондовым методом и сканирующую электронную микроскопию. Рассмотрена особенность кристаллической и аморфной структуры ультратонких волокон на основе поли(3-гидроксибутирата) (ПГБ), содержащего минорные концентрации (0–5%) комплексов тетрафенилпорфирина (ТФП) с марганцем (в форме MnCl2 ), цинком и железом (в форме FeCl3 ). Показано, что при добавлении в волокна ПГБ указанных комплексов меняется морфология волокон, наблюдается изменение кристалличности и замедление молекулярной подвижности в плотных и рыхлых аморфных областях ПГБ в следующей последовательности: ПГБ/ТФП, ПГБ/Zn–ТФП, ПГБ/MnCl2 –ТФП, FeCl3 –ТФП. Температурное воздействие на волокна (их отжиг при 140°С) приводит к резкому росту кристалличности и молекулярной подвижности в аморфных областях волокон. Их экспозиция в водной среде при 70°С приводит к росту энтальпии плавления и замедлению молекулярной динамики только в исходном ПГБ, но к значительному снижению энтальпии в модифицированных волокнах. Молекулярная подвижность цепей в аморфных областях при этом возрастает. Полученные волокнистые материалы обладают бактерицидными свойствами и должны найти применение при создании новых терапевтических систем антибактериального и противоопухолевого действия.

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Tuning the Electronic Properties of Porphyrin Dyes: Effects of meso Substitution on Their Optical and Electrochemical Behaviour

Cited by 33 publications

References 28 publications

Charge recombination losses in thiophene-substituted porphyrin dye-sensitized solar cells

Charge recombination losses in thiophene-substituted porphyrin dye-sensitized solar cells

Mechanical behavior of crystalline ionic porphyrins

Сравнительный Структурно-Динамический Анализ Ультратонких Волокон Поли-(3-Гидроксибутирата), Модифицированного Комплексами Тетрафенилпорфирина С Металлами

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