Home / Publications / New norbornadiene-tethered fulleropyrrolidines

New norbornadiene-tethered fulleropyrrolidines

Arslan Rifkhatovich Akhmetov 1
Arslan Rifkhatovich Akhmetov
, 
Airat Ramilevich Tuktarov 1
Airat Ramilevich Tuktarov
, 
Zarema Rashitovna Sadretdinova 1
Zarema Rashitovna Sadretdinova
, 
Leonard Mukhibovich Khalilov 1
Leonard Mukhibovich Khalilov
, 
10.1016/j.mencom.2020.05.031
Published 2020-04-30
Communication , Volume 30, Issue 3, 352-354
2
Share
Cite this
GOST
 | 
Cite this
GOST Copy
Akhmetov A. R. et al. New norbornadiene-tethered fulleropyrrolidines // Mendeleev Communications. 2020. Vol. 30. No. 3. pp. 352-354.
GOST all authors (up to 50) Copy
Akhmetov A. R., Tuktarov A. R., Sadretdinova Z. R., Khalilov L. M., Dzhemilev U. M. New norbornadiene-tethered fulleropyrrolidines // Mendeleev Communications. 2020. Vol. 30. No. 3. pp. 352-354.
RIS
 | 
Cite this
RIS Copy
TY - JOUR
DO - 10.1016/j.mencom.2020.05.031
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.05.031
TI - New norbornadiene-tethered fulleropyrrolidines
T2 - Mendeleev Communications
AU - Akhmetov, Arslan Rifkhatovich
AU - Tuktarov, Airat Ramilevich
AU - Sadretdinova, Zarema Rashitovna
AU - Khalilov, Leonard Mukhibovich
AU - Dzhemilev, Usein Memetovich
PY - 2020
DA - 2020/04/30
PB - Mendeleev Communications
SP - 352-354
IS - 3
VL - 30
ER -
BibTex
 | 
Cite this
BibTex (up to 50 authors) Copy
@article{2020_Akhmetov,
author = {Arslan Rifkhatovich Akhmetov and Airat Ramilevich Tuktarov and Zarema Rashitovna Sadretdinova and Leonard Mukhibovich Khalilov and Usein Memetovich Dzhemilev},
title = {New norbornadiene-tethered fulleropyrrolidines},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Apr},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.05.031},
number = {3},
pages = {352--354},
doi = {10.1016/j.mencom.2020.05.031}
}
MLA
Cite this
MLA Copy
Akhmetov, Arslan Rifkhatovich, et al. “New norbornadiene-tethered fulleropyrrolidines.” Mendeleev Communications, vol. 30, no. 3, Apr. 2020, pp. 352-354. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.05.031.

Keywords

[3+2]-cycloaddition
azomethine ylides
C60 fullerene
fulleropyrrolidines
norbornadiene
Prato reaction
pyrrolidines
quadricyclane

Abstract

N-Methyl-3,4-fulleropyrrolidine–norbornadiene conjugates with or without (CH2)n (n=0–3) spacers were synthesized by the Prato reaction from the corresponding norbornadiene aldehydes. The influence of the spacer length on the diastereomer composition of the conjugates with two chiral centres studied by 13C NMR revealed a pronounced diastereotopic splitting of the fullerene carbon signals relating to four diastereomers in the case when the norbornadiene substituent was directly attached to the pyrrolidine moiety. When norbornadiene moiety was separated from the pyrrolidine one by three methylene units, the diastereotopic difference was lower and some of the signals were grouped.

References

1.
Photosensitized Isomerization Involving Saturated Centers
Hammond G.S., Wyatt P., DeBoer C.D., Turro N.J.
Journal of the American Chemical Society, 1964
2.
Norbornadiene–quadricyclane — an effective molecular system for the storage of solar energy
Bren' V.A., Dubonosov A.D., Minkin V.I., Chernoivanov V.A.
Russian Chemical Reviews, 1991
3.
Norbornadiene–quadricyclane as an abiotic system for the storage of solar energy
Dubonosov A.D., Bren V.A., Chernoivanov V.A.
Russian Chemical Reviews, 2002
4.
Enthalpy of the metal catalyzed isomerizations of quadricyclane and of tricyclo[4.1.0.02,7]heptane
Wiberg K.B., Connon H.A.
Journal of the American Chemical Society, 1976
6.
Electron Transfer through Norbornadiene and Quadricyclane Moieties as a Model for Molecular Switching
Lainé P., Marvaud V., Gourdon A., Launay J., Argazzi R., Bignozzi C.
Inorganic Chemistry, 1996
8.
Morino S., Watanabe T., Magaya Y., Yamashita T., Horie K., Nishikubo T.
Journal of Photopolymer Science and Technology, 1994
9.
Refractive-index patterning using near-field scanning optical microscopy
Takahashi S., Samata K., Muta H., Machida S., Horie K.
Applied Physics Letters, 2001
10.
Photoresponsive Carboxylic Acids
Herges R., Reif W.
European Journal of Organic Chemistry, 2006
11.
Synthesis of Photoresponsive Polyethers
Starck F., Jones P.G., Herges R.
European Journal of Organic Chemistry, 1998
12.
Preparation and Properties of Photo-Functional Systems with Nitroxide Radicals
Nakatsuji S., Takeuchi S., Ojima T., Ogawa Y., Akutsu H., Yamada J.
Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals, 2001
13.
Preparation and Properties of Some Photo-Responsive Compounds with TEMPO Radical
Takeuchi S., Ogawa Y., Naito A., Sudo K., Yasuoka N., Akutsu H., Yamada J., Nakatsuji S.
Molecular Crystals and Liquid Crystals Science and Technology Section A Molecular Crystals and Liquid Crystals, 2000
14.
Novel photo-responsive organic spin systems: preparation and properties of norbornadienes and spiropyrans with TEMPO radical substituents
Nakatsuji S., Ogawa Y., Takeuchi S., Akutsu H., Yamada J., Naito A., Sudo K., Yasuoka N.
Journal of the Chemical Society Perkin Transactions 2, 2000
16.
An ambipolar organic field-effect transistor using oligothiophene incorporated with two [60]fullerenes
Kunugi Y., Takimiya K., Negishi N., Otsubo T., Aso Y.
Journal of Materials Chemistry A, 2004
17.
Design of fulleropyrrolidine derivatives as an acceptor molecule in a thin layer organic solar cell
Matsumoto K., Hashimoto K., Kamo M., Uetani Y., Hayase S., Kawatsura M., Itoh T.
Journal of Materials Chemistry A, 2010
18.
10.1016/j.mencom.2020.05.031_bib0090
Carini
Handbook of Carbon Nano Materials, 2012
19.
Fullerenes in biology and medicine
Castro E., Garcia A.H., Zavala G., Echegoyen L.
Journal of Materials Chemistry B, 2017
20.
Norbornene, norbornadiene and their derivatives: promising semi-products for organic synthesis and production of polymeric materials
Flid V.R., Gringolts M.L., Shamsiev R.S., Finkelshtein E.S.
Russian Chemical Reviews, 2018
21.
Hydride transfer mechanism in the catalytic allylation of norbornadiene with allyl formate
Durakov S.A., Shamsiev R.S., Flid V.R., Gekhman A.E.
Russian Chemical Bulletin, 2018
22.
Synthesis and Properties of Energy-Rich Methanofullerenes Containing Norbornadiene and Quadricyclane Moieties
Tuktarov A.R., Akhmetov A.R., Khuzin A.A., Dzhemilev U.M.
Journal of Organic Chemistry, 2018
26.
Diastereotopic splitting in the13C NMR spectra of sulfur homofullerenes and methanofullerenes with chiral fragments
Tulyabaev A.R., Tuktarov A.R., Khalilov L.M.
Magnetic Resonance in Chemistry, 2013
27.
Intramolecular 1,3-Dipolar Cycloadditions of Norbornadiene-Tethered Nitrones
Tranmer G.K., Tam W.
Journal of Organic Chemistry, 2001
28.
Nickel-catalyzed [2.pi. + 2.pi. + 2.pi.] (homo-Diels-Alder) and [2.pi. + 2.pi.] cycloadditions of bicyclo[2.2.1]hepta-2,5-dienes.
Lautens M., Edwards L.G., Tam W., Lough A.J.
Journal of the American Chemical Society, 1995
29.
Synthetic Chemistry of Quadricyclane
Petrov V., Vasil'ev N.
Current Organic Synthesis, 2006