Electronic Absorption, Emission and Two-Photon Absorption Properties of Some Functional 1,3,5-Triphenylbenzenes

Suzy L. Streatfield; Claire Pradels; Alphonsine Ngo Ndimba; Nicolas Richy; Anissa Amar; Abdou Boucekkine; Marie P. Cifuentes; Mark G. Humphrey; Olivier Mongin; Frédéric Paul

doi:10.1002/slct.201701653

Electronic Absorption, Emission and Two-Photon Absorption Properties of Some Functional 1,3,5-Triphenylbenzenes

Suzy L. Streatfield, Claire Pradels, Alphonsine Ngo Ndimba, Nicolas Richy, Anissa Amar, Abdou Boucekkine^*, Marie P. Cifuentes, Mark G. Humphrey, Olivier Mongin, Frédéric Paul

^*Corresponding author for this work

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

3 Citations (Scopus)

Abstract

We report herein the linear optical properties of some extended 1,3,5-triphenylbenzene derivatives 1,3,5-[(1, 4-C₆H₄)C≡C(4-C₆H₄X)]₃(C₆H₃) (3-X; X=NO₂, CN, H, OMe, NMe₂, NPh₂) and briefly discuss the two-photon absorption (2PA) cross-sections determined for the derivatives featuring the most electron-rich substituents, contrasting their 2PA performance with the 2PA values previously gathered for their triphenylisocyanurate analogues N,N’,N”-[(1, 4-C₆H₄)C≡C(4-C₆H₄X)]₃(N₃{C(O)}₃) (1-X). When functionalized by electron-releasing substituents at their periphery, 3-X derivatives are potent substitutes for 1-X compounds in NLO applications, especially when maximal transparency is not required in the visible range. Some rationalization of this unexpected outcome is proposed based on DFT calculations.

Original language	English
Pages (from-to)	8080-8085
Number of pages	6
Journal	ChemistrySelect
Volume	2
Issue number	26
DOIs	https://doi.org/10.1002/slct.201701653
Publication status	Published - 11 Sept 2017

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title = "Electronic Absorption, Emission and Two-Photon Absorption Properties of Some Functional 1,3,5-Triphenylbenzenes",

abstract = "We report herein the linear optical properties of some extended 1,3,5-triphenylbenzene derivatives 1,3,5-[(1, 4-C6H4)C≡C(4-C6H4X)]3(C6H3) (3-X; X=NO2, CN, H, OMe, NMe2, NPh2) and briefly discuss the two-photon absorption (2PA) cross-sections determined for the derivatives featuring the most electron-rich substituents, contrasting their 2PA performance with the 2PA values previously gathered for their triphenylisocyanurate analogues N,N{\textquoteright},N”-[(1, 4-C6H4)C≡C(4-C6H4X)]3(N3{C(O)}3) (1-X). When functionalized by electron-releasing substituents at their periphery, 3-X derivatives are potent substitutes for 1-X compounds in NLO applications, especially when maximal transparency is not required in the visible range. Some rationalization of this unexpected outcome is proposed based on DFT calculations.",

keywords = "DFT Calculations, Luminescence, Nonlinear Optical Properties, Triphenylbenzenes, Two-photon Absorption",

author = "Streatfield, {Suzy L.} and Claire Pradels and Ndimba, {Alphonsine Ngo} and Nicolas Richy and Anissa Amar and Abdou Boucekkine and Cifuentes, {Marie P.} and Humphrey, {Mark G.} and Olivier Mongin and Fr{\'e}d{\'e}ric Paul",

note = "Publisher Copyright: {\textcopyright} 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2017",

month = sep,

day = "11",

doi = "10.1002/slct.201701653",

language = "English",

volume = "2",

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journal = "ChemistrySelect",

issn = "2365-6549",

publisher = "Wiley-Blackwell Publishing Ltd",

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TY - JOUR

T1 - Electronic Absorption, Emission and Two-Photon Absorption Properties of Some Functional 1,3,5-Triphenylbenzenes

AU - Streatfield, Suzy L.

AU - Pradels, Claire

AU - Ndimba, Alphonsine Ngo

AU - Richy, Nicolas

AU - Amar, Anissa

AU - Boucekkine, Abdou

AU - Cifuentes, Marie P.

AU - Humphrey, Mark G.

AU - Mongin, Olivier

AU - Paul, Frédéric

PY - 2017/9/11

Y1 - 2017/9/11

N2 - We report herein the linear optical properties of some extended 1,3,5-triphenylbenzene derivatives 1,3,5-[(1, 4-C6H4)C≡C(4-C6H4X)]3(C6H3) (3-X; X=NO2, CN, H, OMe, NMe2, NPh2) and briefly discuss the two-photon absorption (2PA) cross-sections determined for the derivatives featuring the most electron-rich substituents, contrasting their 2PA performance with the 2PA values previously gathered for their triphenylisocyanurate analogues N,N’,N”-[(1, 4-C6H4)C≡C(4-C6H4X)]3(N3{C(O)}3) (1-X). When functionalized by electron-releasing substituents at their periphery, 3-X derivatives are potent substitutes for 1-X compounds in NLO applications, especially when maximal transparency is not required in the visible range. Some rationalization of this unexpected outcome is proposed based on DFT calculations.

AB - We report herein the linear optical properties of some extended 1,3,5-triphenylbenzene derivatives 1,3,5-[(1, 4-C6H4)C≡C(4-C6H4X)]3(C6H3) (3-X; X=NO2, CN, H, OMe, NMe2, NPh2) and briefly discuss the two-photon absorption (2PA) cross-sections determined for the derivatives featuring the most electron-rich substituents, contrasting their 2PA performance with the 2PA values previously gathered for their triphenylisocyanurate analogues N,N’,N”-[(1, 4-C6H4)C≡C(4-C6H4X)]3(N3{C(O)}3) (1-X). When functionalized by electron-releasing substituents at their periphery, 3-X derivatives are potent substitutes for 1-X compounds in NLO applications, especially when maximal transparency is not required in the visible range. Some rationalization of this unexpected outcome is proposed based on DFT calculations.

KW - DFT Calculations

KW - Luminescence

KW - Nonlinear Optical Properties

KW - Triphenylbenzenes

KW - Two-photon Absorption

UR - http://www.scopus.com/inward/record.url?scp=85041704937&partnerID=8YFLogxK

U2 - 10.1002/slct.201701653

DO - 10.1002/slct.201701653

M3 - Article

SN - 2365-6549

VL - 2

SP - 8080

EP - 8085

JO - ChemistrySelect

JF - ChemistrySelect

IS - 26

ER -

Electronic Absorption, Emission and Two-Photon Absorption Properties of Some Functional 1,3,5-Triphenylbenzenes

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