Photochemical site-selective synthesis of [70]methanofullerenes

Sara Vidal; Marta Izquierdo; Wai Kit Law; Kui Jiang; Salvatore Filippone; Josefina Perles; He Yan; Nazario Martin

doi:10.1039/c6cc06072b

Photochemical site-selective synthesis of [70]methanofullerenes

Sara Vidal
, Marta Izquierdo
, Wai Kit Law
, Kui Jiang
, Salvatore Filippone
, Josefina Perles
, He Yan^*
, Nazario Martin^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

16 Citations (Scopus)

Abstract

Methanofullerenes such as the well-known [70]PCBM are commonly synthesized under harsh conditions to obtain the product as a mixture of site-isomers (namely α, β and minor γ) due to the D_5h symmetry of the C₇₀ cage. We report the first site-selective synthesis of [70]methanofullerenes under light irradiation and low temperatures, thus avoiding time-consuming and highly expensive HPLC separations. Pure major site-isomers α-[70]PCBM and α-[70]DPM have been thus efficiently prepared including the crystal structure of 5b. Photovoltaic preliminary results revealed a slightly beneficial performance for α-pure [70]PCBM site-isomer devices.

Original language	English
Pages (from-to)	12733-12736
Number of pages	4
Journal	Chemical Communications
Volume	52
Issue number	86
Online published	3 Oct 2016
DOIs	https://doi.org/10.1039/c6cc06072b
Publication status	Published - 7 Nov 2016
Externally published	Yes

Funding

This work was supported by the European Research Council ERC-320441-Chirallcarbon, Ministerio de Economia y Competitividad (MINECO) of Spain (project CTQ2014-52045-R) and the CAM (FOTOCARBON project S2013/MIT-2841). M. I. thanks the Ministerio de Economia y Competitividad (MINECO) of Spain (Juan de la Cierva-Incorporacion IJCI-2014-19320). N. M. thanks the Alexander von Humboldt Foundation.

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

SDG 7 Affordable and Clean Energy

Research Keywords

HETEROJUNCTION SOLAR-CELLS
POLYMER
PERFORMANCE
MORPHOLOGY
C-70
FULLERENES
VOLTAGE
C-60

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title = "Photochemical site-selective synthesis of [70]methanofullerenes",

abstract = "Methanofullerenes such as the well-known [70]PCBM are commonly synthesized under harsh conditions to obtain the product as a mixture of site-isomers (namely α, β and minor γ) due to the D5h symmetry of the C70 cage. We report the first site-selective synthesis of [70]methanofullerenes under light irradiation and low temperatures, thus avoiding time-consuming and highly expensive HPLC separations. Pure major site-isomers α-[70]PCBM and α-[70]DPM have been thus efficiently prepared including the crystal structure of 5b. Photovoltaic preliminary results revealed a slightly beneficial performance for α-pure [70]PCBM site-isomer devices.",

keywords = "HETEROJUNCTION SOLAR-CELLS, POLYMER, PERFORMANCE, MORPHOLOGY, C-70, FULLERENES, VOLTAGE, C-60",

author = "Sara Vidal and Marta Izquierdo and Law, \{Wai Kit\} and Kui Jiang and Salvatore Filippone and Josefina Perles and He Yan and Nazario Martin",

year = "2016",

month = nov,

day = "7",

doi = "10.1039/c6cc06072b",

language = "English",

volume = "52",

pages = "12733--12736",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "86",

}

TY - JOUR

T1 - Photochemical site-selective synthesis of [70]methanofullerenes

AU - Vidal, Sara

AU - Izquierdo, Marta

AU - Law, Wai Kit

AU - Jiang, Kui

AU - Filippone, Salvatore

AU - Perles, Josefina

AU - Yan, He

AU - Martin, Nazario

PY - 2016/11/7

Y1 - 2016/11/7

N2 - Methanofullerenes such as the well-known [70]PCBM are commonly synthesized under harsh conditions to obtain the product as a mixture of site-isomers (namely α, β and minor γ) due to the D5h symmetry of the C70 cage. We report the first site-selective synthesis of [70]methanofullerenes under light irradiation and low temperatures, thus avoiding time-consuming and highly expensive HPLC separations. Pure major site-isomers α-[70]PCBM and α-[70]DPM have been thus efficiently prepared including the crystal structure of 5b. Photovoltaic preliminary results revealed a slightly beneficial performance for α-pure [70]PCBM site-isomer devices.

AB - Methanofullerenes such as the well-known [70]PCBM are commonly synthesized under harsh conditions to obtain the product as a mixture of site-isomers (namely α, β and minor γ) due to the D5h symmetry of the C70 cage. We report the first site-selective synthesis of [70]methanofullerenes under light irradiation and low temperatures, thus avoiding time-consuming and highly expensive HPLC separations. Pure major site-isomers α-[70]PCBM and α-[70]DPM have been thus efficiently prepared including the crystal structure of 5b. Photovoltaic preliminary results revealed a slightly beneficial performance for α-pure [70]PCBM site-isomer devices.

KW - HETEROJUNCTION SOLAR-CELLS

KW - POLYMER

KW - PERFORMANCE

KW - MORPHOLOGY

KW - C-70

KW - FULLERENES

KW - VOLTAGE

KW - C-60

UR - https://www.scopus.com/pages/publications/84992381714

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0- 84992381714&origin=recordpage

U2 - 10.1039/c6cc06072b

DO - 10.1039/c6cc06072b

M3 - RGC 21 - Publication in refereed journal

SN - 1359-7345

VL - 52

SP - 12733

EP - 12736

JO - Chemical Communications

JF - Chemical Communications

IS - 86

ER -

Photochemical site-selective synthesis of [70]methanofullerenes

Abstract

Funding

UN SDGs

Research Keywords

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