Efficiency enhancement of organic solar cells enabled by interface engineering of sol-gel zinc oxide with an oxadiazole-based material

Fanady, Billy; Song, Wei; Peng, Ruixiang; Wu, Tao; Ge, Ziyi

doi:10.1016/j.orgel.2019.105483

Cited by 23 publications

(14 citation statements)

References 51 publications

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“…Oxadiazoles-five-membered ring heterocycles containing two carbon atoms, two nitrogen atoms, and one oxygen atom-are significant structural elements of organic compounds that are interesting in the fields of industrial materials [1][2][3][4] and biologically active substances [4,5]. Modification of…”

Section: Introductionmentioning

confidence: 99%

Novel 3′-Substituted-1′,2′,4′-Oxadiazole Derivatives of 18βH-Glycyrrhetinic Acid and Their O-Acylated Amidoximes: Synthesis and Evaluation of Antitumor and Anti-Inflammatory Potential In Vitro and In Vivo

Markov

Sen’kova

Popadyuk

et al. 2020

IJMS

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A series of novel 18βH-glycyrrhetinic acid (GA) derivatives containing 3′-(alkyl/phenyl/pyridin(-2″, -3″, and -4″)-yl)-1′,2′,4′-oxadiazole moieties at the C-30 position were synthesized by condensation of triterpenoid’s carboxyl group with corresponding amidoximes and further cyclization. Screening of the cytotoxicity of novel GA derivatives on a panel of tumor cell lines showed that the 3-acetoxy triterpenoid intermediates—O-acylated amidoxime 3a-h—display better solubility under bioassay conditions and more pronounced cytotoxicity compared to their 1′,2′,4′-oxadiazole analogs 4f-h (median IC50 = 7.0 and 49.7 µM, respectively). Subsequent replacement of the 3-acetoxy group by the hydroxyl group of pyridin(-2″, 3″, and -4″)-yl-1′,2′,4′-oxadiazole-bearing GA derivatives produced compounds 5f-h, showing the most pronounced selective toxicity toward tumor cells (median selectivity index (SI) > 12.1). Further detailed analysis of the antitumor activity of hit derivative 5f revealed its marked proapoptotic activity and inhibitory effects on clonogenicity and motility of HeLa cervical carcinoma cells in vitro, and the metastatic growth of B16 melanoma in vivo. Additionally, the comprehensive in silico study revealed intermediate 3d, bearing the tert-butyl moiety in O-acylated amidoxime, as a potent anti-inflammatory candidate, which was able to effectively inhibit inflammatory response induced by IFNγ in macrophages in vitro and carrageenan in murine models in vivo, probably by primary interactions with active sites of MMP9, neutrophil elastase, and thrombin. Taken together, our findings provide a basis for a better understanding of the structure–activity relationship of 1′,2′,4′-oxadiazole-containing triterpenoids and reveal two hit molecules with pronounced antitumor (5f) and anti-inflammatory (3d) activities.

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Section: Introductionmentioning

confidence: 99%

Novel 3′-Substituted-1′,2′,4′-Oxadiazole Derivatives of 18βH-Glycyrrhetinic Acid and Their O-Acylated Amidoximes: Synthesis and Evaluation of Antitumor and Anti-Inflammatory Potential In Vitro and In Vivo

Markov

Sen’kova

Popadyuk

et al. 2020

IJMS

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“…[21,52,53] This increasement is accompanied by an increased J sc (17.56 mA cm À 2 ), an enhanced FF (73.64 %), and a slightly decreased V oc (0.914 V). The noticeable J sc and FF improvements are likely associate with the simultaneously optimized conductivity, surface flatness and γ s of DR-PEDOT : PSS HTL, [24,46,50] while the slight V oc loss seems to be the direct consequence of the slightly lower WF of DR-PEDOT : PSS HTL.…”

Section: Photovoltaic Performance Of Pbdb-t : Itic-based Oscsmentioning

confidence: 98%

“…The lower surface roughness of DR- PEDOT : PSS will produce a more intimate contact with the photoactive layer. [46] The phase image show that PEDOT : PSS film has a coiled-shape structure with weak phase separation between PEDOT and PSS whereas D-PEDOT : PSS film presents massive textures with strong phase separation. The difference in PEDOT grain size may be contributed to the different roughness of PEDOT : PSS and D-PEDOT : PSS films.…”

Section: Effects Of Secondary Doping and Dialysis On The Structure Of Pedot : Pss Blendsmentioning

confidence: 98%

Eliminating the Detrimental Effect of Secondary Doping on PEDOT : PSS Hole Transporting Material Performance

Wang

et al. 2021

ChemSusChem

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Secondary doping has a long history of use in conductivity enhancement in poly (3,4-ethylenedioxythiophene) : poly(styrene sulfonate) (PEDOT : PSS). However, very little research has addressed its detrimental effect on application performance of PEDOT : PSS in organic solar cells. Herein, it was shown that the uneven drying of secondary dopant-water mixture results in a nonuniform/continuous film structure, causing severe damage to the device efficiencies (dropping about 8 and 23 % for poly [(2,6-(4,8-bis(5-(2-ethylhexyl) and poly[(2,6-(4,8-bis(5-(2) cells, respectively) and thermal stabilities. Moreover, a simple yet robust dialysis treatment was proposed to solve the issue of noncontinuity and retain the secondary doping's advantages of quinoid structure simultaneously, thus demonstrating a significant enhancement in device performance. This study will be of great importance to the future exploration of the next generation of post-treatment strategy.

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“…The hydrophobic nature of the CB molecule has a secondary beneficial effect, depressing the absorption of external agents such as moisture within the layer. A better charge transport ability is also achieved by means of an oxadiazole-based electron-transporting material, PBD, placed between the ZnO ETL and the photoactive layer [181]. Consequently, PCE increases from 10.8% to 11.6%, due to the simultaneous enhancement in J sc and FF.…”

Section: Cbsmentioning

confidence: 99%

Tackling Performance Challenges in Organic Photovoltaics: An Overview about Compatibilizers

et al. 2020

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Organic Photovoltaics (OPVs) based on Bulk Heterojunction (BHJ) blends are a mature technology. Having started their intensive development two decades ago, their low cost, processability and flexibility rapidly funneled the interest of the scientific community, searching for new solutions to expand solar photovoltaics market and promote sustainable development. However, their robust implementation is hampered by some issues, concerning the choice of the donor/acceptor materials, the device thermal/photo-stability, and, last but not least, their morphology. Indeed, the morphological profile of BHJs has a strong impact over charge generation, collection, and recombination processes; control over nano/microstructural morphology would be desirable, aiming at finely tuning the device performance and overcoming those previously mentioned critical issues. The employ of compatibilizers has emerged as a promising, economically sustainable, and widely applicable approach for the donor/acceptor interface (D/A-I) optimization. Thus, improvements in the global performance of the devices can be achieved without making use of more complex architectures. Even though several materials have been deeply documented and reported as effective compatibilizing agents, scientific reports are quite fragmentary. Here we would like to offer a panoramic overview of the literature on compatibilizers, focusing on the progression documented in the last decade.

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Efficiency enhancement of organic solar cells enabled by interface engineering of sol-gel zinc oxide with an oxadiazole-based material

Cited by 23 publications

References 51 publications

Novel 3′-Substituted-1′,2′,4′-Oxadiazole Derivatives of 18βH-Glycyrrhetinic Acid and Their O-Acylated Amidoximes: Synthesis and Evaluation of Antitumor and Anti-Inflammatory Potential In Vitro and In Vivo

Novel 3′-Substituted-1′,2′,4′-Oxadiazole Derivatives of 18βH-Glycyrrhetinic Acid and Their O-Acylated Amidoximes: Synthesis and Evaluation of Antitumor and Anti-Inflammatory Potential In Vitro and In Vivo

Eliminating the Detrimental Effect of Secondary Doping on PEDOT : PSS Hole Transporting Material Performance

Tackling Performance Challenges in Organic Photovoltaics: An Overview about Compatibilizers

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