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Formation of [18]trannulenes derived via Bingel reactions between C60F18O isomers and CHBr(CO2Et)(2) and between C60F18 and CHX(CO2R)(2) (X = Br, Cl; R = Me, Et)

Formation of [18]trannulenes derived via Bingel reactions between C60F18O isomers and CHBr(CO2Et)(2) and between C60F18 and CHX(CO2R)(2) (X = Br, Cl; R = Me, Et)
Formation of [18]trannulenes derived via Bingel reactions between C60F18O isomers and CHBr(CO2Et)(2) and between C60F18 and CHX(CO2R)(2) (X = Br, Cl; R = Me, Et)
Through extended S(N)2' nucleophilic substitution of three fluorine atoms in two isomers of C60F18O by alkyl halogenomalonate anions -CBr(CO2Et)(2), (obtained from diethyl bromomalonate in the presence of DBU) we have prepared and characterised the [18]trannulenes, C60F15O[CBr(CO2Et)(2)](3). Likewise we have prepared [18]trannulenes by the reactions between C60F18 and either -CBr(CO2Me)(2) or -CCl(CO2Et)(2) (obtained from the corresponding esters 1, 2 and DBU). The formation of the trannulenes from either 1 or 2 shows that the CBr(CO2Me)(2) and CCl(CO2Et)(2) substituents, though smaller than CBr(CO2Et)(2) are still large enough to bring about the extended S(N)2' substitution, rather than direct nucleophilic substitution. The products from the oxides show that oxygen does not inhibit trannulene formation either sterically or electronically. Each derivative has the brilliant emerald-green colour of the corresponding [18]trannulene prepared from C60F18 and diethyl bromomalonate, arising from the presence of bands at ca. 615 and 660 nm; minor variations in wavenumber and relative intensities occur according to the derivative. Under less forcing conditions, mono- and bis-substitution products were obtained from the more available symmetrical oxide and from the reaction of the chloro- and bromo-esters with C60F18.
fullerene porphyrin dyad, charge-transfer, photophysical properties, electron-transfer, energy-transfer, building-block, c-60, competition
1364-5471
1118-1121
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Kuvytchko, Igor V.
fa975688-666e-4bc1-b8bd-d3e94cb39fe5
Wei, Xian-Wen
76b952ea-9f76-41de-be81-91f46652c927
Boltalina, Olga V.
7fefd47c-6427-4d51-8d9f-e1b116daad8c
Gol'dt, Ilya V.
92aef798-e0b7-4dea-a3b5-178093f24ce8
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Darwish, Adam D.
25f723f4-6a72-4e21-a361-76b275b617ef
Kuvytchko, Igor V.
fa975688-666e-4bc1-b8bd-d3e94cb39fe5
Wei, Xian-Wen
76b952ea-9f76-41de-be81-91f46652c927
Boltalina, Olga V.
7fefd47c-6427-4d51-8d9f-e1b116daad8c
Gol'dt, Ilya V.
92aef798-e0b7-4dea-a3b5-178093f24ce8
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6

Darwish, Adam D., Kuvytchko, Igor V., Wei, Xian-Wen, Boltalina, Olga V., Gol'dt, Ilya V., Street, Joan M. and Taylor, Roger (2002) Formation of [18]trannulenes derived via Bingel reactions between C60F18O isomers and CHBr(CO2Et)(2) and between C60F18 and CHX(CO2R)(2) (X = Br, Cl; R = Me, Et). Journal of the Chemical Society, Perkin Transactions 2, (6), 1118-1121. (doi:10.1039/b201155g).

Record type: Article

Abstract

Through extended S(N)2' nucleophilic substitution of three fluorine atoms in two isomers of C60F18O by alkyl halogenomalonate anions -CBr(CO2Et)(2), (obtained from diethyl bromomalonate in the presence of DBU) we have prepared and characterised the [18]trannulenes, C60F15O[CBr(CO2Et)(2)](3). Likewise we have prepared [18]trannulenes by the reactions between C60F18 and either -CBr(CO2Me)(2) or -CCl(CO2Et)(2) (obtained from the corresponding esters 1, 2 and DBU). The formation of the trannulenes from either 1 or 2 shows that the CBr(CO2Me)(2) and CCl(CO2Et)(2) substituents, though smaller than CBr(CO2Et)(2) are still large enough to bring about the extended S(N)2' substitution, rather than direct nucleophilic substitution. The products from the oxides show that oxygen does not inhibit trannulene formation either sterically or electronically. Each derivative has the brilliant emerald-green colour of the corresponding [18]trannulene prepared from C60F18 and diethyl bromomalonate, arising from the presence of bands at ca. 615 and 660 nm; minor variations in wavenumber and relative intensities occur according to the derivative. Under less forcing conditions, mono- and bis-substitution products were obtained from the more available symmetrical oxide and from the reaction of the chloro- and bromo-esters with C60F18.

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Published date: 2002
Keywords: fullerene porphyrin dyad, charge-transfer, photophysical properties, electron-transfer, energy-transfer, building-block, c-60, competition

Identifiers

Local EPrints ID: 19718
URI: http://eprints.soton.ac.uk/id/eprint/19718
ISSN: 1364-5471
PURE UUID: b273dc75-77f4-4c57-b8d5-22b261bee1fb

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Date deposited: 17 Feb 2006
Last modified: 15 Jul 2019 19:26

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Contributors

Author: Adam D. Darwish
Author: Igor V. Kuvytchko
Author: Xian-Wen Wei
Author: Olga V. Boltalina
Author: Ilya V. Gol'dt
Author: Joan M. Street
Author: Roger Taylor

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