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Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers?

Research output: Contribution to Journal/Magazine › Journal article › peer-review

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Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers? / La Rosa, Andrea; Gillemot, Katalin; Leary, Edmund et al.
In: Journal of Organic Chemistry, Vol. 79, No. 11, 06.06.2014, p. 4871-4877.

Research output: Contribution to Journal/Magazine › Journal article › peer-review

Harvard

La Rosa, A, Gillemot, K, Leary, E, Evangeli, C, Teresa Gonzalez, M, Filippone, S, Rubio-Bollinger, G, Agrait, N, Lambert, CJ & Martin, N 2014, 'Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers?', Journal of Organic Chemistry, vol. 79, no. 11, pp. 4871-4877. https://doi.org/10.1021/jo500342x

APA

La Rosa, A., Gillemot, K., Leary, E., Evangeli, C., Teresa Gonzalez, M., Filippone, S., Rubio-Bollinger, G., Agrait, N., Lambert, C. J., & Martin, N. (2014). Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers? Journal of Organic Chemistry, 79(11), 4871-4877. https://doi.org/10.1021/jo500342x

Vancouver

La Rosa A, Gillemot K, Leary E, Evangeli C, Teresa Gonzalez M, Filippone S et al. Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers? Journal of Organic Chemistry. 2014 Jun 6;79(11):4871-4877. doi: 10.1021/jo500342x

Author

La Rosa, Andrea ; Gillemot, Katalin ; Leary, Edmund et al. / Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers?. In: Journal of Organic Chemistry. 2014 ; Vol. 79, No. 11. pp. 4871-4877.

Bibtex

@article{845638515a8649498521ff312aee22c8,
title = "Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers?",
abstract = "Two C-60 dumbbell molecules have been synthesized containing either cyclopropane or pyrrolidine rings connecting two fullerenes to a central fluorene core. A combination of spectroscopic techniques reveals that the cyclopropane dumbbell possesses better electronic communication between the fullerenes and the fluorene. This observation is underpinned by DFT transport calculations, which show that the cyclopropane dumbbell gives a higher calculated single-molecule conductance, a result of an energetically lower-lying LUMO level that extends deeper into the backbone. This strengthens the idea that cyclopropane behaves as a quasi-double bond.",
keywords = "HETEROJUNCTION SOLAR-CELLS, FULLERENE DERIVATIVES, ELECTROCHEMISTRY, ORGANOFULLERENES, SYSTEMS",
author = "{La Rosa}, Andrea and Katalin Gillemot and Edmund Leary and Charalambos Evangeli and {Teresa Gonzalez}, Maria and Salvatore Filippone and Gabino Rubio-Bollinger and Nicolas Agrait and Lambert, {Colin J.} and Nazario Martin",
year = "2014",
month = jun,
day = "6",
doi = "10.1021/jo500342x",
language = "English",
volume = "79",
pages = "4871--4877",
journal = "Journal of Organic Chemistry",
issn = "0022-3263",
publisher = "American Chemical Society",
number = "11",

}

RIS

TY - JOUR

T1 - Does a cyclopropane ring enhance the electronic communication in dumbbell-type C-60 dimers?

AU - La Rosa, Andrea

AU - Gillemot, Katalin

AU - Leary, Edmund

AU - Evangeli, Charalambos

AU - Teresa Gonzalez, Maria

AU - Filippone, Salvatore

AU - Rubio-Bollinger, Gabino

AU - Agrait, Nicolas

AU - Lambert, Colin J.

AU - Martin, Nazario

PY - 2014/6/6

Y1 - 2014/6/6

N2 - Two C-60 dumbbell molecules have been synthesized containing either cyclopropane or pyrrolidine rings connecting two fullerenes to a central fluorene core. A combination of spectroscopic techniques reveals that the cyclopropane dumbbell possesses better electronic communication between the fullerenes and the fluorene. This observation is underpinned by DFT transport calculations, which show that the cyclopropane dumbbell gives a higher calculated single-molecule conductance, a result of an energetically lower-lying LUMO level that extends deeper into the backbone. This strengthens the idea that cyclopropane behaves as a quasi-double bond.

AB - Two C-60 dumbbell molecules have been synthesized containing either cyclopropane or pyrrolidine rings connecting two fullerenes to a central fluorene core. A combination of spectroscopic techniques reveals that the cyclopropane dumbbell possesses better electronic communication between the fullerenes and the fluorene. This observation is underpinned by DFT transport calculations, which show that the cyclopropane dumbbell gives a higher calculated single-molecule conductance, a result of an energetically lower-lying LUMO level that extends deeper into the backbone. This strengthens the idea that cyclopropane behaves as a quasi-double bond.

KW - HETEROJUNCTION SOLAR-CELLS

KW - FULLERENE DERIVATIVES

KW - ELECTROCHEMISTRY

KW - ORGANOFULLERENES

KW - SYSTEMS

U2 - 10.1021/jo500342x

DO - 10.1021/jo500342x

M3 - Journal article

VL - 79

SP - 4871

EP - 4877

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

SN - 0022-3263

IS - 11

ER -