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Structure-Property Relationships for the Electronic Applications of Bis-Adduct Isomers of Phenyl-C₆₁ Butyric Acid Methyl Ester.

ABSTRACT: Higher adducts of a fullerene, such as the bis-adduct of PCBM (bis-PCBM), can be used to achieve shallower molecular orbital energy levels than, for example, PCBM or C_60. Substituting the bis-adduct for the parent fullerene is useful to increase the open-circuit voltage of organic solar cells or achieve better energy alignment as electron transport layers in, for example, perovskite solar cells. However, bis-PCBM is usually synthesized as a mixture of structural isomers, which can lead to both energetic and morphological disorder, negatively affecting device performance. Here, we present a comprehensive study on the molecular properties of 19 pure bis-isomers of PCBM using a variety of characterization methods, including ultraviolet photoelectron spectroscopy, thermal gravimetric analysis, differential scanning calorimetry, single crystal structure, and (time-dependent) density functional theory calculation. We find that the lowest unoccupied molecular orbital of such bis-isomers can be tuned to be up to 170 meV shallower than PCBM and up to 100 meV shallower than the mixture of unseparated isomers. The isolated bis-isomers also show an electron mobility in organic field-effect transistors of up to 4.5 × 10^-2 cm²/(V s), which is an order of magnitude higher than that of the mixture of bis-isomers. These properties enable the fabrication of the highest performing bis-PCBM organic solar cell to date, with the best device showing a power conversion efficiency of 7.2%. Interestingly, we find that the crystallinity of bis-isomers correlates negatively with electron mobility and organic solar cell device performance, which we relate to their molecular symmetry, with a lower symmetry leading to more amorphous bis-isomers, less energetic disorder, and higher dimensional electron transport. This work demonstrates the potential of side chain engineering for optimizing the performance of fullerene-based organic electronic devices.

SUBMITTER: Hou X

PROVIDER: S-EPMC10782444 | biostudies-literature | 2024 Jan

REPOSITORIES: biostudies-literature

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Structure-Property Relationships for the Electronic Applications of Bis-Adduct Isomers of Phenyl-C<sub>61</sub> Butyric Acid Methyl Ester.

Hou Xueyan X Coker Jack F JF Yan Jun J Shi Xingyuan X Azzouzi Mohammed M Eisner Flurin D FD McGettrick James D JD Tuladhar Sachetan M SM Abrahams Isaac I Frost Jarvist M JM Li Zhe Z Dennis T John S TJS Nelson Jenny J

Chemistry of materials : a publication of the American Chemical Society 20231228 1

Higher adducts of a fullerene, such as the bis-adduct of PCBM (bis-PCBM), can be used to achieve shallower molecular orbital energy levels than, for example, PCBM or C<sub>60.</sub> Substituting the bis-adduct for the parent fullerene is useful to increase the open-circuit voltage of organic solar cells or achieve better energy alignment as electron transport layers in, for example, perovskite solar cells. However, bis-PCBM is usually synthesized as a mixture of structural isomers, which can lea ...[more]

PMID: 38222935

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Project description:The magnetoconductance (MC) effect was investigated for two types of organic solar cells with single junction (SJ) and bulk junction (BJ) of poly(3-hexylthiophene) (P3HT) as donor (D) and [6,6]-phenyl-C61-butyric acid methyl ester (PCBM) as acceptor (A). Three components with different half-field-at-half-maximums (B 1/2) of 4 ± 1, 20 ± 15 and >400 mT, hereafter referred to MCS,M,B in a sequence, were observed in the magnetic field dependence of the MC effects measured under dark and light conditions. The magnitude of the MCS,M,B components is sensitive to not only the junction structure of the cell but also the presence or absence of incident light. The bias voltage (V) dependence of the MC effect in the dark for the SJ-cell is maximized around the turn-on voltage (V ON) of the dark current, where a flat band condition of the active layer is achieved. The B 1/2 for the MCM component of the SJ-cell increases with V beyond V ON. In light, the BJ-cell exhibits the MC effect, whereas no effect is detected for the SJ-cell. The MCS,M components for the BJ-cell in light increase with the incident light power. The transient MCS,M components for the BJ-cell measured using a nanosecond pulse laser increases with the delay time after the flash. By integrating these phenomena and the phase of the MC effect, it is concluded that all of the MC components arise from the magnetic field effect on the spin conversion of nongeminate electron (e)-hole (h) pairs with spin-dependent charge recombinations at the D/A-interface. The B 1/2 values for MCS,M,B are, respectively, understood by the spin conversion due to the hyperfine interaction, the spin relaxation, and the g-factor difference for e (PCBM-) and h (P3HT+). Kinetic simulations of the MCS,M components for the BJ-cell observed at the short-circuit condition in light yield an efficiency of ca. 40% for the nongeminate recombination, which is accompanied by the generation of triplet excitons as well as relaxation to a ground singlet state. The loss mechanism of moderate triplet recombination suggests an important possibility to improve the power conversion efficiency by harvesting of the triplet excitons.

Project description:The demand for new ionic liquid (IL)-based systems to selectively sequester carbon dioxide from gas mixtures has prompted the development of individual components involving the tailored design of IL themselves or solid-supported materials that provide excellent gas permeability of the overall material as well as the ability to incorporate large amounts of ionic liquid. In this work, novel IL-encapsulated microparticles comprising a cross-linked copolymer shell of β-myrcene and styrene and a hydrophilic core of the ionic liquid 1-ethyl-3-methylimidazolium dicyanamide ([EMIM][DCA]) are proposed as viable materials for CO2 capture. Water-in-oil (w/o) emulsion polymerization of different mass ratios of β-myrcene to styrene (i.e. 100/0, 70/30, 50/50, 0/100) yielded IL-encapsulated microparticles, where the encapsulation efficiency of [EMIM][DCA] was dependent on the copolymer shell composition. Thermal analysis using thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC) revealed that both thermal stability and glass transition temperatures depend on the mass ratio of β-myrcene to styrene. Images from scanning electron microscopy (SEM) and transmission electron microscopy (TEM) were used to observe the microparticle shell morphology as well as measure the particle size perimeter. Particle sizes were found to be between 5 and 44 μm. CO2 sorption experiments were conducted gravimetrically using TGA instrumentation. Interestingly, a trade-off between CO2 absorption capacity and ionic liquid encapsulation was observed. While increasing the β-myrcene content within the microparticle shell increases the amount of encapsulated [EMIM][DCA], the observed CO2 absorption capacity did not increase as expected due to reduced porosity compared to microparticles with higher styrene content in the microparticle shell. [EMIM][DCA] microcapsules with a 50/50 weight ratio of β-myrcene/styrene showed the best synergistic effect between spherical particle diameter (32.2 μm), pore size (0.75 μm), and high CO2 sorption capacity of ∼0.5 mmol CO2/g sample within a short absorption period of 20 min. Therefore, core-shell microcapsules composed of β-myrcene and styrene are envisioned as a promising material for CO2 sequestration applications.

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Structure-Property Relationships for the Electronic Applications of Bis-Adduct Isomers of Phenyl-C₆₁ Butyric Acid Methyl Ester.

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Structure-Property Relationships for the Electronic Applications of Bis-Adduct Isomers of Phenyl-C<sub>61</sub> Butyric Acid Methyl Ester.

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Structure-Property Relationships for the Electronic Applications of Bis-Adduct Isomers of Phenyl-C61 Butyric Acid Methyl Ester.

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Structure-Property Relationships for the Electronic Applications of Bis-Adduct Isomers of Phenyl-C<sub>61</sub> Butyric Acid Methyl Ester.

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OmicsDI is part of the ELIXIR infrastructure

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Structure-Property Relationships for the Electronic Applications of Bis-Adduct Isomers of Phenyl-C₆₁ Butyric Acid Methyl Ester.