Preparation and characterisation of the C60 charge transfer complex C60−.[1,1′,3,3′-tetramethyl-Δ2,2′-bi(imidazolidine)]+.

Schilder, A.; Gotschy, B.; Seidl, Angelika; Gompper, Rudolf

doi:10.1016/0301-0104(95)00013-e

Cited by 11 publications

(16 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Importantly, the high stability of the radical ion pairs in [4] •+ ⊂[C60] •− is highlighted upon comparison with previous studies into the interaction of C60 and simple organic amine donors that reported significant air and moisture sensitivity 116 of the C60 •− generated with t½ = 10 -30 mins. 133,134,136 After three days the complex solution returned to its original green colour (Figure 5a) and the Vis-NIR absorption spectrum predominantly resembled that of the 'neutral' Green Box and C60 fullerene species, i.e. reforming [4] δ+ ⊂[C60] δ− (Figure S4.10-4.11).…”

Section: Nitrobenzenementioning

confidence: 98%

“…This remarkable durability of the radical ions in solution prompted a more detailed kinetic study by Vis-NIR absorption, EPR and NMR spectroscopies. A time course measurement of the electronic absorption band associated with [PDI] •+ at λabs = 890 nm of a 1:5 host:guest stoichiometric mixture revealed fast SET followed by a slow decrease in concentration of this species over seven hours, 123,133,134 giving a PDI radical cation half-life of t½ > 600 minutes with radical ions still apparent in the NIR spectrum after two days (Figure S7.1). 135 Under the same conditions the time dependence of the EPR spectrum revealed similar kinetic behaviour for C60 •− (Figures S6.3, S7.2).…”

Section: Nitrobenzenementioning

confidence: 99%

See 1 more Smart Citation

The Green Box: An Electronically Versatile Perylene Diimide Macrocyclic Host for Fullerenes

et al. 2019

View full text Add to dashboard Cite

The powerful electron accepting ability of fullerenes makes them ubiquitous components in biomimetic donor-acceptor systems that model the intermolecular electron transfer processes of Nature's photosynthetic centre. Exploiting perylene diimides (PDIs) as components in cyclic host systems for the noncovalent recognition of fullerenes is unprecedented, in part because archetypal PDIs are also electron deficient, making dyad assembly formation electronically unfavourable. To address this, we report the strategic design and synthesis of a novel large, macrocyclic receptor comprised of two covalently strapped electron-rich bis-pyrrolidine PDI panels, nicknamed the "Green Box" due to its colour. Through the principle of electronic complementarity, the Green Box exhibits strong recognition of pristine fullerenes (C60/70), with the non-covalent ground and excited state interactions that occur upon fullerene guest encapsulation characterised by a range of techniques including electronic absorption, fluorescence emission, NMR and time-resolved EPR spectroscopies, cyclic voltammetry and mass spectrometry. Whilst relatively low polarity solvents result in partial charge transfer in the host donor-guest acceptor complex, increasing the polarity of the solvent medium facilitates rare, thermally allowed full electron transfer from Green Box to fullerene in the ground state. Both species in the ensuing charge separated radical ion paired complex are spectroscopically characterised, with thermodynamic reversibility and significant kinetic stability also demonstrated. Importantly, the Green Box represents a seminal type of C60/70 host where electron-rich PDI motifs are utilised as recognition motifs for fullerenes, facilitating novel intermolecular, solvent tuneable ground state electronic communication with these guests. The ability to switch between extremes of the charge transfer energy continuum is without precedent in synthetic fullerene-based dyads.

show abstract

Section: Nitrobenzenementioning

confidence: 98%

Section: Nitrobenzenementioning

confidence: 99%

The Green Box: An Electronically Versatile Perylene Diimide Macrocyclic Host for Fullerenes

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Another ferromagnetic fulleride phase was believed to have formed with C 60 and the strongly reducing 1,1′,3,3′-tetramethyl-∆2,2′-bi(imidazolidine), 164 but this was later shown to a be diamagnetic material, possibly containing a mixture of C 60 -and C 60 2-ions. 165 Primary amines such as 1-amino-3-propanol and 1,5-diaminopentane are reported to give (-1) and (-2) ions of C 60 and C 70 . 166,167 Pyridine is a useful extractant for liberating endohedral fullerenes from metallofullerene soot.…”

Section: Coordination and Organometallic Compounds As Reducing Agmentioning

confidence: 99%

Discrete Fulleride Anions and Fullerenium Cations

2000

View full text Add to dashboard Cite

His research interests include reactive cation and superacid chemistry with inert carborane counterions, ionic liquids, bioinorganic chemistry, spin-coupling phenomena, fullerene chemistry, and new carbon-or porphyrin-based materials. He is a Sloan Fellow, a Dreyfus Teacher−Scholar Awardee, and a Guggenheim Fellow. Robert Bolskar received his B.S. degree in Chemistry from Carroll College in Waukesha, WI, in 1992. He earned his Ph.D. degree at the University of Southern California in Los Angeles under the direction of Christopher Reed in 1997, investigating the synthetic redox chemistry of fullerene anions and cations. In 1998 he moved to the University of California, Riverside, as Managing Research Associate. He is currently Senior Chemist at TDA Research in Wheat Ridge, CO. His research interests include the chemistry and physics of fullerene compounds, supramolecular chemistry, strongly oxidizing systems, and electrophilic cations.

show abstract

“…They are ionic fullerene complexes with tetrakis(dimethylamino)ethylene (TDAE) and its analogs (2,14), and neutral complexes of C 60 with porphyrazine, (15) tetraphenylporphyrin, (16,17) N,N,N 0 , N 0 -tetramethyl-p-phenylenediamine (TMPDA) (18), azotriptycene, (19) and 4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-one (20).…”

Section: Introductionmentioning

confidence: 99%