Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene

Andrew J. Peloquin; Rebecca L. Stone; Sarah E. Avila; Erlyn R. Rudico; Christopher B. Horn; Kim A. Gardner; Jane E.B. Johnson; Scott T. Iacono; Gary J. Balaich

doi:10.1021/jo301101x

Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene

Andrew J. Peloquin
, Rebecca L. Stone
, Sarah E. Avila
, Erlyn R. Rudico
, Christopher B. Horn
, Kim A. Gardner
, Jane E.B. Johnson
, Scott T. Iacono
, Gary J. Balaich

United States Air Force Academy

Research output: Contribution to journal › Article › peer-review

Abstract

The synthesis, structural, and electronic properties of nine 1,3-diphenyl-6-alkyl/aryl substituted pentafulvenes were studied. Pyrene ring π–π interactions were revealed from analysis of the experimental crystal packing of 1,3-diphenyl-6-(1-pyrene)fulvene and supporting DFT calculations. Photophysical properties derived from UV–vis and fluorescence emission measurements demonstrated tunable and low HOMO–LUMO band gaps for the series. The presented results point to a model synthetic approach for incorporation of extended π systems and donor-π-acceptor groups for fulvene-based electronic materials.

Original language	American English
Journal	Journal of Organic Chemistry
Volume	77
DOIs	https://doi.org/10.1021/jo301101x
State	Published - Jan 1 2012
Externally published	Yes

Disciplines

Organic Chemistry

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http://dx.doi.org/10.1021/jo301101x

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Peloquin, A. J., Stone, R. L., Avila, S. E., Rudico, E. R., Horn, C. B., Gardner, K. A., Johnson, J. E. B., Iacono, S. T., & Balaich, G. J. (2012). Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene. Journal of Organic Chemistry, 77. https://doi.org/10.1021/jo301101x

@article{aee06bd05f8241c1ae04a014f08dbe75,

title = "Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene",

abstract = " The synthesis, structural, and electronic properties of nine 1,3-diphenyl-6-alkyl/aryl substituted pentafulvenes were studied. Pyrene ring π–π interactions were revealed from analysis of the experimental crystal packing of 1,3-diphenyl-6-(1-pyrene)fulvene and supporting DFT calculations. Photophysical properties derived from UV–vis and fluorescence emission measurements demonstrated tunable and low HOMO–LUMO band gaps for the series. The presented results point to a model synthetic approach for incorporation of extended π systems and donor-π-acceptor groups for fulvene-based electronic materials.",

author = "Peloquin, \{Andrew J.\} and Stone, \{Rebecca L.\} and Avila, \{Sarah E.\} and Rudico, \{Erlyn R.\} and Horn, \{Christopher B.\} and Gardner, \{Kim A.\} and Johnson, \{Jane E.B.\} and Iacono, \{Scott T.\} and Balaich, \{Gary J.\}",

note = "Peloquin, A. J.; Stone, R. L.; Avila, S. E.; Rudico, E. R.; Horn, C. B.; Gardner, K. A.; Ball, D. W.; Johnson, J. E. B.; Iacono, S. T.; Balaich, G. J. Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene. J. Org. Chem. 2012, 77, 6371-6376.",

year = "2012",

month = jan,

day = "1",

doi = "10.1021/jo301101x",

language = "American English",

volume = "77",

journal = "Journal of Organic Chemistry",

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TY - JOUR

T1 - Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene

AU - Peloquin, Andrew J.

AU - Stone, Rebecca L.

AU - Avila, Sarah E.

AU - Rudico, Erlyn R.

AU - Horn, Christopher B.

AU - Gardner, Kim A.

AU - Johnson, Jane E.B.

AU - Iacono, Scott T.

AU - Balaich, Gary J.

N1 - Peloquin, A. J.; Stone, R. L.; Avila, S. E.; Rudico, E. R.; Horn, C. B.; Gardner, K. A.; Ball, D. W.; Johnson, J. E. B.; Iacono, S. T.; Balaich, G. J. Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene. J. Org. Chem. 2012, 77, 6371-6376.

PY - 2012/1/1

Y1 - 2012/1/1

N2 - The synthesis, structural, and electronic properties of nine 1,3-diphenyl-6-alkyl/aryl substituted pentafulvenes were studied. Pyrene ring π–π interactions were revealed from analysis of the experimental crystal packing of 1,3-diphenyl-6-(1-pyrene)fulvene and supporting DFT calculations. Photophysical properties derived from UV–vis and fluorescence emission measurements demonstrated tunable and low HOMO–LUMO band gaps for the series. The presented results point to a model synthetic approach for incorporation of extended π systems and donor-π-acceptor groups for fulvene-based electronic materials.

AB - The synthesis, structural, and electronic properties of nine 1,3-diphenyl-6-alkyl/aryl substituted pentafulvenes were studied. Pyrene ring π–π interactions were revealed from analysis of the experimental crystal packing of 1,3-diphenyl-6-(1-pyrene)fulvene and supporting DFT calculations. Photophysical properties derived from UV–vis and fluorescence emission measurements demonstrated tunable and low HOMO–LUMO band gaps for the series. The presented results point to a model synthetic approach for incorporation of extended π systems and donor-π-acceptor groups for fulvene-based electronic materials.

UR - https://engagedscholarship.csuohio.edu/scichem_facpub/105

UR - http://dx.doi.org/10.1021/jo301101x

U2 - 10.1021/jo301101x

DO - 10.1021/jo301101x

M3 - Article

VL - 77

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

ER -

Synthesis of 1,3-Diphenyl-6-alkyl/aryl-Substituted Fulvene Chromophores: Observation of π–π Interactions in a 6-Pyrene-Substituted 1,3-Diphenylfulvene

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