The bis-linking of tetrathiafulvalene (TTF) to C60: Towards the control of electron transfer between π-donors and C60

Boulle, C.; Rabreau, J.M.; Hudhomme, Piétrick; Cariou, M.; Jubault, M.; Gorgues, A.; Orduna, Jesús; Garı́n, Javier

doi:10.1016/s0040-4039(97)00759-4

Cited by 67 publications

(23 citation statements)

References 11 publications

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“…With the aim of promoting an ICT process by providing a more rigid spatial orientation of the HOMO of the TTF addend with respect to the LUMO of the C 60 moiety, [48] Rovira and co-workers [49] and Hudhomme and co-workers [50] synthesized derivatives 29 and 30, respectively, in which TTF is attached to C 60 by two s-bonds (formed by a Diels±Alder reaction of transient 4,5-dimethylene-TTF onto C 60 ). UV-vis spectroscopic and CV data for 29 and 30 again implied no electron transfer within the molecules, although an EPR spectrum of the latter compound suggested that electron spins were present, although their origin was not established.…”

Section: Fullerene Acceptorsmentioning

confidence: 99%

“…UV-vis spectroscopic and CV data for 29 and 30 again implied no electron transfer within the molecules, although an EPR spectrum of the latter compound suggested that electron spins were present, although their origin was not established. [50] Rovira and co-workers have recently performed more detailed physicochemical studies on the series of monoadducts 29, 31, and 32, and the bis-adduct 33.…”

Section: Fullerene Acceptorsmentioning

confidence: 99%

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Tetrathiafulvalenes as π-Electron Donors for Intramolecular Charge-Transfer Materials

Bryce

1999

Adv. Mater.

334

144

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Although tetrathiafulvalene (TTF) and its derivatives have been extensively studied for more than 25 years as p-electron donors in intermolecular charge-transfer materials, the intriguing potential of TTF as a donor in an intramolecular sense has only recently been developed. Many versatile, functionalized TTF building blocks are now readily available, and this article will review a range of compounds in which TTF is covalently linked to an electron acceptor moiety by a variety of linking units, sometimes giving rise to an intramolecular charge-transfer (ICT) interaction, which is most frequently manifested in the optical and electrochemical properties. In this context, acceptor subunits include: tetracyano-p-quinodimethane, quinones, electrondeficient aryl groups, pyridinium and bipyridinium units, fullerenes, phthalocyanines, and mesomerically conjugated carbonyl, thiocarbonyl, ester, and related groups. This work paves the way for more systematic and detailed studies of TTF±spacer±A molecules (where A is an acceptor) in which there is increased control of the structural, electronic, optical, and magnetic properties arising from ICT interactions in the ground state, or in the excited state.

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Section: Fullerene Acceptorsmentioning

confidence: 99%

Section: Fullerene Acceptorsmentioning

confidence: 99%

Tetrathiafulvalenes as π-Electron Donors for Intramolecular Charge-Transfer Materials

Bryce

1999

Adv. Mater.

334

144

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“…The possibility of developing dienic chemistry in the TTF series was missing until two different strategies were presented by the groups of Angers (route A) [48,51] and Barcelona (route B) [45,52]. Route A used the known detailed synthesis of 2,3-bis (methyloxycarbonyl)TTF.…”

Section: Diels-alder Reaction For Linking Ttf Onto C60mentioning

confidence: 99%

“…Not long after, we were interested in the synthesis of the C60-TTF-C60 dumbbell 37 [51]. However, this research area was limited by lack of suitable TTF building blocks able to generate tetramethylidene[4H]-TTF.…”

Section: Diels-alder Cycloaddition For the Synthesis Of Dumbbellsmentioning

confidence: 99%

Diels–Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60

Hudhomme

2006

Comptes Rendus. Chimie

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“…There are two main objectives concerning organic functionalization of C 60 and other fullerenes: one is focused on modification of some of their properties for easier handling, and the other one involves combination of the fullerene properties with those of other materials. To promote electronic interactions, the Angers [8,9] and Barcelona [10,11] groups have adopted the strategy of linking C 60 and TTFs by a rigid bridge. Electron transfer processes play an important role in numerous applications of C 60 -derived materials.…”

Section: Introductionmentioning

confidence: 99%

SPECTRAL STUDIES OF THEBIS-LINKED TETRATHIAFULVALENES (TTFs) TO [60]FULLERENE

Olejniczak¹,

Bogucki²,

Golub³

et al. 2002

Fullerenes, Nanotubes and Carbon Nanostructures

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Results of the first extended spectral investigation of the bis-linked tetrathiafulvalene donors (TTFs) to [60]fullerene are reported. From UV-VIS-NIR-IR spectra it is stated that charge distribution on C 60 moiety and on TTFs attachments is disturbed after the adduct formation. This redistribution depends not only on the nature of an attached molecular group but also on the number of bounded donors. In the infrared spectra of the bisadducts, a particularly strong resonant effect was observed.

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The bis-linking of tetrathiafulvalene (TTF) to C60: Towards the control of electron transfer between π-donors and C60

Cited by 67 publications

References 11 publications

Tetrathiafulvalenes as π-Electron Donors for Intramolecular Charge-Transfer Materials

Tetrathiafulvalenes as π-Electron Donors for Intramolecular Charge-Transfer Materials

Diels–Alder cycloaddition as an efficient tool for linking π-donors onto fullerene C60

SPECTRAL STUDIES OF THEBIS-LINKED TETRATHIAFULVALENES (TTFs) TO [60]FULLERENE

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