C–N linked donor type porphyrin derivatives: unrevealed hole-transporting materials for efficient hybrid perovskite solar cells

Reis, Melani J. A.; Nogueira, Ana T.; Eulálio, Ana; Moura, Nuno M. M.; Rodrigues, Joana; Ivanou, Dzmitry; Abreu, Paulo E.; Correia, M. R.; Neves, Maria da Graça; Pereira, Ana; Mendes, Adélio

doi:10.1039/d3dt00512g

Cited by 4 publications

(2 citation statements)

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“…Reis et al prepared a Zn(II) porphyrin complex incorporating carbazole units at 10,20- meso positions through a nucleophilic substitution reaction mediated by PhI(OAc) 2 /NaAuCl 4 ·2H 2 O (Scheme ). The analogous Cu(II) was prepared using either an Ullmann or a Buchwald–Hartwig C–N transition-metal-assisted coupling . Incorporation of carbazole units at the porphyrin was highly influenced by the electronic environment at the porphyrinic core.…”

Section: Htms Obtained Via Postfunctionalization Of 515-a2-porphyrinsmentioning

confidence: 99%

“…The analogous Cu(II) was prepared using either an Ullmann or a Buchwald–Hartwig C–N transition-metal-assisted coupling. 38 Incorporation of carbazole units at the porphyrin was highly influenced by the electronic environment at the porphyrinic core. The Zn(II) complex showed metal replacement issues when the reaction was carried out under Pd-mediated Buchwald–Hartwig or Cu-mediated Ullmann conditions, resulting mainly in the exchange of Zn(II) with Pd(II) or Cu(II), respectively.…”

Section: Htms Obtained Via Postfunctionalization Of 515-a 2...mentioning

confidence: 99%

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Porphyrin-Based Hole-Transporting Materials for Perovskite Solar Cells: Boosting Performance with Smart Synthesis

Reis,

Pereira,

Moura

et al. 2024

ACS Omega

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Perovskite solar cells (PSCs) are becoming a promising and revolutionary advancement within the photovoltaic field globally. Continuous improvement in efficiency, straightforward processing methods, and use of lightweight and cost-effective materials represent superior features, among other notable aspects. Still, long-term stability and durability are issues to address to facilitate widespread commercial adoption and practical application prospects. Research has focused on overcoming these challenges, and charge transport materials play a critical role in determining charge dynamics, photovoltaic performance, and device stability. Conventional hole-transporting materials (HTMs), spiro-OMe-TAD and PTAA, contribute to remarkable power conversion efficiencies owing to high thin-film quality and matched energy alignment. However, they often show a high material cost, low carrier mobility, and poor stability, which greatly limit their practical applications. Now, this review outlines recent advances in synthetic approaches to porphyrin-based HTMs to tune the charge dynamics by optimizing their molecular structures and properties. The main structural features comprise porphyrins of A 4 -type, trans A 2 B 2 -type, and photosynthetic pigment analogues. Strategies include well-established routes to provide the required macrocycles, such as condensation of pyrrole or dipyrromethanes with suitable aldehydes, metalation of the porphyrin inner core, and postfunctionalization of peripheral positions. These functionalizations involve conventional procedures (e.g., halogenation, esterification, transesterification, nucleophilic oxidation, reduction, and nucleophilic substitution) as well as metal-catalyzed ones such as Suzuki−Miyaura, Sonogashira, Buchwald−Hartwig, and Ullmann cross-coupling reactions. As HTMs can also protect the perovskite layer from the external environment, porphyrin structures play a pivotal role in chemical, mechanical, and environmental stability, with their high hydrophobicity ability as the most significant parameter. The impact of porphyrins on the hole hopping of other HTMs while acting as an additive or an interlayer, passivating defects, and improving charge transport is also highlighted to provide real insights into ways to develop efficient and stable porphyrin-based materials for PSCs. This perspective aims to guide the scientific community in the design of new porphyrin molecules to place PSCs as an outperformer in photovoltaic technologies.

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Section: Htms Obtained Via Postfunctionalization Of 515-a2-porphyrinsmentioning

confidence: 99%

Section: Htms Obtained Via Postfunctionalization Of 515-a 2...mentioning

confidence: 99%