A faux hawk fullerene with PCBM-like properties.

التفاصيل البيبلوغرافية
العنوان:	A faux hawk fullerene with PCBM-like properties.
المؤلفون:	San LK; Department of Chemistry , Colorado State University , Fort Collins , CO 80523 , USA . Email: olga.boltalina@colostate.edu ; Email: steven.strauss@colostate.edu., Bukovsky EV; Department of Chemistry , Colorado State University , Fort Collins , CO 80523 , USA . Email: olga.boltalina@colostate.edu ; Email: steven.strauss@colostate.edu., Larson BW; Department of Chemistry , Colorado State University , Fort Collins , CO 80523 , USA . Email: olga.boltalina@colostate.edu ; Email: steven.strauss@colostate.edu.; National Renewable Energy Laboratory , Golden , CO 80401 , USA . Email: nikos.kopidakis@nrel.gov ; Email: garry.rumbles@nrel.gov., Whitaker JB; Department of Chemistry , Colorado State University , Fort Collins , CO 80523 , USA . Email: olga.boltalina@colostate.edu ; Email: steven.strauss@colostate.edu., Deng SHM; Physical Sciences Division , Pacific Northwest National Laboratory , MS K8-88, P.O. Box 999 , Richland , WA 99352 , USA . Email: xuebin.wang@pnnl.gov., Kopidakis N; National Renewable Energy Laboratory , Golden , CO 80401 , USA . Email: nikos.kopidakis@nrel.gov ; Email: garry.rumbles@nrel.gov., Rumbles G; National Renewable Energy Laboratory , Golden , CO 80401 , USA . Email: nikos.kopidakis@nrel.gov ; Email: garry.rumbles@nrel.gov., Popov AA; Leibniz Institute for Solid State and Materials Research , 01069 Dresden , Germany . Email: a.popov@ifw-dresden.de., Chen YS; ChemMatCARS Beamline , University of Chicago Advanced Photon Source , Argonne , IL 60439 , USA . Email: yschen@cars.uchicago.edu., Wang XB; Physical Sciences Division , Pacific Northwest National Laboratory , MS K8-88, P.O. Box 999 , Richland , WA 99352 , USA . Email: xuebin.wang@pnnl.gov., Boltalina OV; Department of Chemistry , Colorado State University , Fort Collins , CO 80523 , USA . Email: olga.boltalina@colostate.edu ; Email: steven.strauss@colostate.edu., Strauss SH; Department of Chemistry , Colorado State University , Fort Collins , CO 80523 , USA . Email: olga.boltalina@colostate.edu ; Email: steven.strauss@colostate.edu.
المصدر:	Chemical science [Chem Sci] 2015 Mar 01; Vol. 6 (3), pp. 1801-1815. Date of Electronic Publication: 2014 Dec 16.
نوع المنشور:	Journal Article
اللغة:	English
بيانات الدورية:	Publisher: Royal Society of Chemistry Country of Publication: England NLM ID: 101545951 Publication Model: Print-Electronic Cited Medium: Print ISSN: 2041-6520 (Print) Linking ISSN: 20416520 NLM ISO Abbreviation: Chem Sci Subsets: PubMed not MEDLINE
أسماء مطبوعة:	Original Publication: Cambridge, UK : Royal Society of Chemistry, [2010]-
مستخلص:	Reaction of C 60 , C 6 F 5 CF 2 I, and SnH( n -Bu) 3 produced, among other unidentified fullerene derivatives, the two new compounds 1,9-C 60 (CF 2 C 6 F 5 )H ( 1 ) and 1,9-C 60 ( cyclo -CF 2 (2-C 6 F 4 )) ( 2 ). The highest isolated yield of 1 was 35% based on C 60 . 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 C 60 . Compound 1 is thermally stable in 1,2-dichlorobenzene (oDCB) at 160 °C but was rapidly converted to 2 upon addition of Sn 2 ( 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/C 6 D 6 by addition of stoichiometric, or sub-stoichiometric, amounts of proton sponge (PS) or cobaltocene (CoCp 2 ). DFT calculations indicate that when 1 is deprotonated, the anion C 60 (CF 2 C 6 F 5 ) ^- can undergo facile intramolecular S N Ar 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 S N Ar 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 C 60 and higher by 0.18(1) eV than the EA of phenyl-C 61 -butyric acid methyl ester (PCBM). In contrast, the relative E 1/2 (0/-) values of 2 and C 60 , -0.01(1) and 0.00(1) V, respectively, are virtually the same (on this scale, and under the same conditions, the E 1/2 (0/-) of PCBM is -0.09 V). Time-resolved microwave conductivity charge-carrier yield × 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.
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تواريخ الأحداث:	Date Created: 20171117 Latest Revision: 20231112
رمز التحديث:	20231112
مُعرف محوري في PubMed:	PMC5653957
DOI:	10.1039/c4sc02970d
PMID:	29142669
قاعدة البيانات:	MEDLINE

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تدمد:	2041-6520
DOI:	10.1039/c4sc02970d