Separation and identification of indene–C<sub>70</sub> bisadduct isomers

Zhang, Bolong; Subbiah, Jegadesan; Jones, David J.; Wong, Wallace W. H.

doi:10.3762/bjoc.12.88

Cited by 7 publications

(15 citation statements)

References 21 publications

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“…Variability of the π‐system topology in the trifluoromethylated isomers is reflected in the electronic absorption spectra, and the characteristic spectral features can be of assistance in the task of structural identification. More, importantly, the UV/Vis spectroscopic properties are of key significance with regard to optoelectronic applications . The spectra of the individual C 70 (CF 3 ) n compounds considered in the present study are shown in Figures S9–S13 in the Supporting Information.…”

Section: Resultssupporting

confidence: 85%

“…More, importantly,t he UV/Vis spectroscopic properties are of key significance with regard to optoelectronic applications. [12,[45][46][47][48][49][50] The spectra of the individual C 70 (CF 3 ) n compounds considered in the presents tudy are showni nF iguresS9-S13 in the Supporting Information. Except for the isomers 12-I and 12-II,t he spectra of which coincide with those previously reported, [11,12] the spectroscopic data are reported for the first time.…”

Section: Uv/vis Spectroscopy and Band Gapsmentioning

confidence: 99%

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Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Kosaya

Rybalchenko

Lukonina

et al. 2018

Chemistry An Asian Journal

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We survey the structure and electronic properties of the family of higher trifluoromethylated C (CF ) molecules with n=14, 16, 18, and 20. Twenty-two available compounds, of which thirteen are newly obtained and characterized, demonstrate the broad diversity of π-system topologies, which enabled us to study the interplay between the CF addition pattern and the electronic properties. UV/Vis spectroscopic and cyclic voltammetric studies demonstrate the importance of the exact addition pattern rather than the plain number of addends. Of particular interest is the skew pentagonal pyramid (SPP) addition pattern, which enables formation of closed-shell cyclopentadienyl anions C (CF ) through CF detachment upon electron transfer. A detailed study of the process is presented for a SPP-C (CF ) where potentiostatic electrolysis at the second reduction potential gives C (CF ) oxidizable to a persistent C (CF ) radical. Together with the literature data for the lower C (CF ) compounds with n=2-12, the present results show good correlation between the experimental boundary level positions and the DFT predictions. The compounds turn out to be electron acceptor molecular semiconductors with experimental LUMO energies and HOMO-LUMO gaps within the ranges of -4.3 to -3.7 eV and 1.6 to 3.3 eV, respectively, depending on the shape of the conjugated fragments. The HOMO levels fall within the range of -5.6 to -6.9 eV and show linear correlation with the number of addends.

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Section: Resultssupporting

confidence: 85%

Section: Uv/vis Spectroscopy and Band Gapsmentioning

confidence: 99%

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Kosaya

Rybalchenko

Lukonina

et al. 2018

Chemistry An Asian Journal

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“…[35][36][37] Isolated single IC70BA isomers have been shown to alter the device PCE. [38] However, there is little information on how a mixture of regio-isomers affects the device output. To address this point, we produced a number of standard architecture PSCs (Figure 1d and 1e) using processing conditions tailored for a IC70BA sample with a fixed regio-isomeric distribution (hereafter IC70BA#1), and then transferred this knowledge to another IC70BA sample (hereafter IC70BA#2) exhibiting a dissimilar regio-isomeric distribution, in order to investigate the importance of the regio-isomerism on the vertical phase separation of the P3HT:IC70BA BHJ.…”

Section: Introductionmentioning

confidence: 99%

Achieving 6.7% Efficiency in P3HT/Indene‐C₇₀ Bisadduct Solar Cells through the Control of Vertical Volume Fraction Distribution and Optimized Regio‐Isomer Ratios

Kutsarov

Rašović

Zachariadis

et al. 2016

Adv Elect Materials

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Indene C60 and C70 bisadducts (IC60BA and IC70BA) have relatively high lowest unoccupied molecular orbital energies. In poly(3‐hexylthiophene) (P3HT)‐based polymer solar cells (PSCs), this produces an increase in open‐circuit voltage (VOC) and power conversion efficiency (PCE). However, ICBA synthesis produces a mixture of regio‐isomers with different indene spatial orientations (2, 5, and 12 o'clock) that alter the IC70BA molecular packing when mixed with P3HT. In this paper, how the IC70BA regio‐isomerism affects the PSC performance is examined by investigating the molecular packing of P3HT:IC70BA layers with different regio‐isomeric ratios. For the first time, non‐destructive spectroscopic ellipsometry is used to investigate the effect of the fabrication conditions on the P3HT/IC70BA vertical volume fraction distribution and the results are attributed to the spatial arrangement of the regio‐isomers. It is demonstrated that this unambiguously affects the PSC performance. As a result, record device efficiencies are repeatedly attained for standard architecture P3HT:IC70BA PSCs with photoactive areas of 0.43 cm2, achieving 5.9 (±0.4)% PCE (n = 15). With control of the IC70BA constituent, device PCEs vary from below 2.2% to peak values above 6.7%, among the highest recorded PCEs for a P3HT combination, highlighting the importance of the molecular phase separation for high‐efficiency devices.

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“…In general, the C 60 bisadducts were more deeply studied. Comparative studies on OSCs utilizing the purified C 70 bisadducts have appeared very recently. − To study a relation between anisotropy and OSC efficacies in the present work, we have calculated anisotropies of polarizability of the C 70 derivatives tested in the above-cited works and collated the computational results with the corresponding PCE measurements.…”

Section: Introductionmentioning

confidence: 99%

The C₇₀ Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics

Sabirov

2016

J. Phys. Chem. C

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Currently, higher fullerene adducts (bis-, tris-, and multiadducts) come into use as electron acceptor components for organic solar cells (OSCs) with enhanced output parameters. These compounds have numerous positional isomers, and isomerism crucially influences the performances of photovoltaic devices. Indeed, application of the isolated and purified fullerene adducts (isomer-free fullerene-adduct OSCs) allows increasing power conversion efficiency (PCE) compared to the use of the isomeric mixtures. Previously, we have found that OSCs reveal higher PCE if they utilize the C 60 bisadducts with the lowest anisotropy of polarizability. To demonstrate a general nature of the found correlation in the present work, we have theoretically studied anisotropy of polarizability of the selected isomeric C 70 mono-, bis-, and higher adducts synthesized and separately tested as OSC electron acceptors in recent experimental works. We have found that, as in the case of C 60 , less-anisotropic C 70 derivatives reveal higher PCE of the corresponding photovoltaic devices. Thus, the correlation between anisotropy of polarizability of fullerene acceptors and power conversion efficiency of OSC based on them has a general nature (regardless of the fullerene type and nature of addends), and we can formulate the minimum anisotropy hypothesis: f ullerene adducts with low anisotropy of polarizability are more ef f icient as electron acceptor materials for organic solar cells than their highly anisotropic regioisomers. This conjecture is supported with congruence of relevant experimental and computational data with scarce exceptions and may be recommended as an auxiliary tool for the molecular design and screening of novel fullerene derivatives promising for organic solar cells. The reasons for the importance of polarizability (and its anisotropy) underlying this principle are discussed.

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Separation and identification of indene–C₇₀ bisadduct isomers

Cited by 7 publications

References 21 publications

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Achieving 6.7% Efficiency in P3HT/Indene‐C₇₀ Bisadduct Solar Cells through the Control of Vertical Volume Fraction Distribution and Optimized Regio‐Isomer Ratios

The C₇₀ Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics

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Separation and identification of indene–C70 bisadduct isomers

Cited by 7 publications

References 21 publications

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Facile Separation, Spectroscopic Identification, and Electrochemical Properties of Higher Trifluoromethylated Derivatives of [70]Fullerene

Achieving 6.7% Efficiency in P3HT/Indene‐C70 Bisadduct Solar Cells through the Control of Vertical Volume Fraction Distribution and Optimized Regio‐Isomer Ratios

The C70 Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics

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Separation and identification of indene–C₇₀ bisadduct isomers

Achieving 6.7% Efficiency in P3HT/Indene‐C₇₀ Bisadduct Solar Cells through the Control of Vertical Volume Fraction Distribution and Optimized Regio‐Isomer Ratios

The C₇₀ Fullerene Adducts with Low Anisotropy of Polarizability are More Efficient Electron Acceptors for Organic Solar Cells. The Minimum Anisotropy Hypothesis for Efficient Isomer-Free Fullerene-Adduct Photovoltaics