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Title: A faux hawk fullerene with PCBM-like properties

Abstract

Reaction of C60, C6F5CF2I, and SnH(n-Bu)3 produced, among other unidentified fullerene derivatives, the two new compounds 1,9-C60(CF2C6F5)H (1) and 1,9-C60(cyclo-CF2(2-C6F4)) (2). The highest isolated yield of 1 was 35% based on C60. Depending on the reaction conditions, the relative amounts of 1 and 2 generated in situ were as high as 85% and 71%, respectively, based on HPLC peak integration and summing over all fullerene species present other than unreacted C60. Compound 1 is thermally stable in 1,2-dichlorobenzene (oDCB) at 160 °C but was rapidly converted to 2 upon addition of Sn2(n-Bu)6 at this temperature. In contrast, complete conversion of 1 to 2 occurred within minutes, or hours, at 25 °C in 90/10 (v/v) PhCN/C6D6 by addition of stoichiometric, or sub-stoichiometric, amounts of proton sponge (PS) or cobaltocene (CoCp2). DFT calculations indicate that when 1 is deprotonated, the anion C60(CF2C6F5)- can undergo facile intramolecular SNAr annulation to form 2 with concomitant loss of F-. To our knowledge this is the first observation of a fullerene-cage carbanion acting as an SNAr nucleophile towards an aromatic C–F bond. The gas-phase electron affinity (EA) of 2 was determined to be 2.805(10) eV by low-temperature PES, higher by 0.12(1) eV than the EA ofmore » C60 and higher by 0.18(1) eV than the EA of phenyl-C61-butyric acid methyl ester (PCBM). In contrast, the relative E1/2(0/-) values of 2 and C60, -0.01(1) and 0.00(1) V, respectively, are virtually the same (on this scale, and under the same conditions, the E1/2(0/-) of PCBM is -0.09 V). Time-resolved microwave conductivity charge-carrier yield x mobility values for organic photovoltaic active-layer-type blends of 2 and poly-3-hexylthiophene (P3HT) were comparable to those for equimolar blends of PCBM and P3HT. The structure of solvent-free crystals of 2 was determined by single-crystal X-ray diffraction. The number of nearest-neighbor fullerene–fullerene interactions with centroid∙∙∙centroid (⊙∙∙∙⊙) distances of ≤ 10.34 Å is significantly greater, and the average ⊙∙∙∙⊙ distance is shorter, for 2 (10 nearest neighbors; ave. ⊙∙∙∙⊙ distance = 10.09 Å) than for solvent-free crystals of PCBM (7 nearest neighbors; ave. ⊙∙∙∙⊙ distance = 10.17 Å). Finally, the thermal stability of 2 was found to be far greater than that of PCBM.« less

Authors:
 [1];  [1];  [2];  [1];  [3];  [4];  [4];  [5];  [6];  [3];  [1];  [1]
  1. Colorado State Univ., Fort Collins, CO (United States)
  2. Colorado State Univ., Fort Collins, CO (United States); National Renewable Energy Lab. (NREL), Golden, CO (United States)
  3. Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
  4. National Renewable Energy Lab. (NREL), Golden, CO (United States)
  5. Leibniz Inst. for Solid State and Materials Research (IFW), Dresden (Germany)
  6. Univ. of Chicago Advanced Photon Source, Argonne, IL (United States)
Publication Date:
Research Org.:
Argonne National Lab. (ANL), Argonne, IL (United States). Advanced Photon Source (APS); National Renewable Energy Lab. (NREL), Golden, CO (United States); Pacific Northwest National Lab. (PNNL), Richland, WA (United States). Environmental Molecular Sciences Lab. (EMSL)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
OSTI Identifier:
1171261
Alternate Identifier(s):
OSTI ID: 1184288; OSTI ID: 1220716
Report Number(s):
PNNL-SA-105706; NREL/JA-5900-64001
Journal ID: ISSN 2041-6539
Grant/Contract Number:  
AC02-06CH11357; AC36-08GO28308; AC05-76RL01830
Resource Type:
Accepted Manuscript
Journal Name:
Chemical Science (Online)
Additional Journal Information:
Journal Name: Chemical Science (Online); Journal Volume: 6; Journal Issue: 3; Journal ID: ISSN 2041-6539
Publisher:
Royal Society of Chemistry
Country of Publication:
United States
Language:
ENGLISH
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; nucleophilic aromatic substitution; heptafluorobenzyl; perfluorobenzyl; fullerene; hydrofullerene; electron affinity; DFT; OPV; organic photovoltaic; time-resolved microwave conductivity; X-ray crystallography; PCBM; Environmental Molecular Sciences Laboratory; 14 SOLAR ENERGY; 77 NANOSCIENCE AND NANOTECHNOLOGY; fullerene derivatives

Citation Formats

San, Long K., Bukovsky, Eric V., Larson, Bryon W., Whitaker, James B., Deng, S. H.M., Kopidakis, Nikos, Rumbles, Garry, Popov, Alexey A., Chen, Yu-Sheng, Wang, Xue-Bin, Boltalina, Olga V., and Strauss, Steven H.. A faux hawk fullerene with PCBM-like properties. United States: N. p., 2014. Web. https://doi.org/10.1039/C4SC02970D.
San, Long K., Bukovsky, Eric V., Larson, Bryon W., Whitaker, James B., Deng, S. H.M., Kopidakis, Nikos, Rumbles, Garry, Popov, Alexey A., Chen, Yu-Sheng, Wang, Xue-Bin, Boltalina, Olga V., & Strauss, Steven H.. A faux hawk fullerene with PCBM-like properties. United States. https://doi.org/10.1039/C4SC02970D
San, Long K., Bukovsky, Eric V., Larson, Bryon W., Whitaker, James B., Deng, S. H.M., Kopidakis, Nikos, Rumbles, Garry, Popov, Alexey A., Chen, Yu-Sheng, Wang, Xue-Bin, Boltalina, Olga V., and Strauss, Steven H.. Tue . "A faux hawk fullerene with PCBM-like properties". United States. https://doi.org/10.1039/C4SC02970D. https://www.osti.gov/servlets/purl/1171261.
@article{osti_1171261,
title = {A faux hawk fullerene with PCBM-like properties},
author = {San, Long K. and Bukovsky, Eric V. and Larson, Bryon W. and Whitaker, James B. and Deng, S. H.M. and Kopidakis, Nikos and Rumbles, Garry and Popov, Alexey A. and Chen, Yu-Sheng and Wang, Xue-Bin and Boltalina, Olga V. and Strauss, Steven H.},
abstractNote = {Reaction of C60, C6F5CF2I, and SnH(n-Bu)3 produced, among other unidentified fullerene derivatives, the two new compounds 1,9-C60(CF2C6F5)H (1) and 1,9-C60(cyclo-CF2(2-C6F4)) (2). The highest isolated yield of 1 was 35% based on C60. Depending on the reaction conditions, the relative amounts of 1 and 2 generated in situ were as high as 85% and 71%, respectively, based on HPLC peak integration and summing over all fullerene species present other than unreacted C60. Compound 1 is thermally stable in 1,2-dichlorobenzene (oDCB) at 160 °C but was rapidly converted to 2 upon addition of Sn2(n-Bu)6 at this temperature. In contrast, complete conversion of 1 to 2 occurred within minutes, or hours, at 25 °C in 90/10 (v/v) PhCN/C6D6 by addition of stoichiometric, or sub-stoichiometric, amounts of proton sponge (PS) or cobaltocene (CoCp2). DFT calculations indicate that when 1 is deprotonated, the anion C60(CF2C6F5)- can undergo facile intramolecular SNAr annulation to form 2 with concomitant loss of F-. To our knowledge this is the first observation of a fullerene-cage carbanion acting as an SNAr nucleophile towards an aromatic C–F bond. The gas-phase electron affinity (EA) of 2 was determined to be 2.805(10) eV by low-temperature PES, higher by 0.12(1) eV than the EA of C60 and higher by 0.18(1) eV than the EA of phenyl-C61-butyric acid methyl ester (PCBM). In contrast, the relative E1/2(0/-) values of 2 and C60, -0.01(1) and 0.00(1) V, respectively, are virtually the same (on this scale, and under the same conditions, the E1/2(0/-) of PCBM is -0.09 V). Time-resolved microwave conductivity charge-carrier yield x mobility values for organic photovoltaic active-layer-type blends of 2 and poly-3-hexylthiophene (P3HT) were comparable to those for equimolar blends of PCBM and P3HT. The structure of solvent-free crystals of 2 was determined by single-crystal X-ray diffraction. The number of nearest-neighbor fullerene–fullerene interactions with centroid∙∙∙centroid (⊙∙∙∙⊙) distances of ≤ 10.34 Å is significantly greater, and the average ⊙∙∙∙⊙ distance is shorter, for 2 (10 nearest neighbors; ave. ⊙∙∙∙⊙ distance = 10.09 Å) than for solvent-free crystals of PCBM (7 nearest neighbors; ave. ⊙∙∙∙⊙ distance = 10.17 Å). Finally, the thermal stability of 2 was found to be far greater than that of PCBM.},
doi = {10.1039/C4SC02970D},
journal = {Chemical Science (Online)},
number = 3,
volume = 6,
place = {United States},
year = {2014},
month = {12}
}

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Figure 1 Figure 1: OLYP DFT-optimized structure of 1,9-C60(CF2C6F5)H (1) and the X-ray structure of 1,9-C60(cyclo-CF2(2-C6F4)) (2; 50% probability ellipsoids). Only the major twin portion of the X-ray structure is shown. The shape of compound 2 is reminiscent of a hairstyle known as the faux hawk, as shown in Fig. S-1.†

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