Tampere University of Technology

TUTCRIS Research Portal

π-Expanded α,β-unsaturated ketones: Synthesis, optical properties, and two-photon-induced polymerization

Research output: Contribution to journalArticleScientificpeer-review

Standard

π-Expanded α,β-unsaturated ketones : Synthesis, optical properties, and two-photon-induced polymerization. / Nazir, Rashid; Bourquard, Florent; Balčiūnas, Evaldas; Smoleń, Sabina; Gray, David; Tkachenko, Nikolai V.; Farsari, Maria; Gryko, Daniel T.

In: ChemPhysChem, Vol. 16, No. 3, 2015, p. 682–690.

Research output: Contribution to journalArticleScientificpeer-review

Harvard

Nazir, R, Bourquard, F, Balčiūnas, E, Smoleń, S, Gray, D, Tkachenko, NV, Farsari, M & Gryko, DT 2015, 'π-Expanded α,β-unsaturated ketones: Synthesis, optical properties, and two-photon-induced polymerization', ChemPhysChem, vol. 16, no. 3, pp. 682–690. https://doi.org/10.1002/cphc.201402646

APA

Nazir, R., Bourquard, F., Balčiūnas, E., Smoleń, S., Gray, D., Tkachenko, N. V., ... Gryko, D. T. (2015). π-Expanded α,β-unsaturated ketones: Synthesis, optical properties, and two-photon-induced polymerization. ChemPhysChem, 16(3), 682–690. https://doi.org/10.1002/cphc.201402646

Vancouver

Author

Nazir, Rashid ; Bourquard, Florent ; Balčiūnas, Evaldas ; Smoleń, Sabina ; Gray, David ; Tkachenko, Nikolai V. ; Farsari, Maria ; Gryko, Daniel T. / π-Expanded α,β-unsaturated ketones : Synthesis, optical properties, and two-photon-induced polymerization. In: ChemPhysChem. 2015 ; Vol. 16, No. 3. pp. 682–690.

Bibtex - Download

@article{ae39cb5f506b4d9cbc7f8f377c32b766,
title = "π-Expanded α,β-unsaturated ketones: Synthesis, optical properties, and two-photon-induced polymerization",
abstract = "A library of π-expanded α,β-unsaturated ketones was designed and synthesized. They were prepared by a combination of Wittig reaction, Sonogashira reaction, and aldol condensation. It was further demonstrated that the double aldol condensation can be performed effectively for highly polarized styrene- and diphenylacetylene-derived aldehydes. The strategic placement of two dialkylamino groups at the periphery of D-π-A-π-D molecules resulted in dyes with excellent solubility. These ketones absorb light in the region 400-550nm. Many of them display strong solvatochromism so that the emission ranges from 530-580nm in toluene to the near-IR region in benzonitrile. Ketones based on cyclobutanone as central moieties display very high fluorescence quantum yields in nonpolar solvents, which decrease drastically in polar media. Photophysical studies of these new functional dyes revealed that they possess an enhanced two-photon absorption cross section when compared with simpler ketone derivatives. Due to strong polarization of the resulting dyes, values of two-photon absorption cross sections on the level of 200-300GM at 800nm were achieved, and thanks to that as well as the presence of the keto group, these new two-photon initiators display excellent performance so that the operating region is 5-75mW in some cases.",
keywords = "Aldol reaction, Ketones, Photosensitizers, Polymerization, Two-photon absorption",
author = "Rashid Nazir and Florent Bourquard and Evaldas Balčiūnas and Sabina Smoleń and David Gray and Tkachenko, {Nikolai V.} and Maria Farsari and Gryko, {Daniel T.}",
year = "2015",
doi = "10.1002/cphc.201402646",
language = "English",
volume = "16",
pages = "682–690",
journal = "ChemPhysChem",
issn = "1439-4235",
publisher = "Wiley-VCH Verlag",
number = "3",

}

RIS (suitable for import to EndNote) - Download

TY - JOUR

T1 - π-Expanded α,β-unsaturated ketones

T2 - Synthesis, optical properties, and two-photon-induced polymerization

AU - Nazir, Rashid

AU - Bourquard, Florent

AU - Balčiūnas, Evaldas

AU - Smoleń, Sabina

AU - Gray, David

AU - Tkachenko, Nikolai V.

AU - Farsari, Maria

AU - Gryko, Daniel T.

PY - 2015

Y1 - 2015

N2 - A library of π-expanded α,β-unsaturated ketones was designed and synthesized. They were prepared by a combination of Wittig reaction, Sonogashira reaction, and aldol condensation. It was further demonstrated that the double aldol condensation can be performed effectively for highly polarized styrene- and diphenylacetylene-derived aldehydes. The strategic placement of two dialkylamino groups at the periphery of D-π-A-π-D molecules resulted in dyes with excellent solubility. These ketones absorb light in the region 400-550nm. Many of them display strong solvatochromism so that the emission ranges from 530-580nm in toluene to the near-IR region in benzonitrile. Ketones based on cyclobutanone as central moieties display very high fluorescence quantum yields in nonpolar solvents, which decrease drastically in polar media. Photophysical studies of these new functional dyes revealed that they possess an enhanced two-photon absorption cross section when compared with simpler ketone derivatives. Due to strong polarization of the resulting dyes, values of two-photon absorption cross sections on the level of 200-300GM at 800nm were achieved, and thanks to that as well as the presence of the keto group, these new two-photon initiators display excellent performance so that the operating region is 5-75mW in some cases.

AB - A library of π-expanded α,β-unsaturated ketones was designed and synthesized. They were prepared by a combination of Wittig reaction, Sonogashira reaction, and aldol condensation. It was further demonstrated that the double aldol condensation can be performed effectively for highly polarized styrene- and diphenylacetylene-derived aldehydes. The strategic placement of two dialkylamino groups at the periphery of D-π-A-π-D molecules resulted in dyes with excellent solubility. These ketones absorb light in the region 400-550nm. Many of them display strong solvatochromism so that the emission ranges from 530-580nm in toluene to the near-IR region in benzonitrile. Ketones based on cyclobutanone as central moieties display very high fluorescence quantum yields in nonpolar solvents, which decrease drastically in polar media. Photophysical studies of these new functional dyes revealed that they possess an enhanced two-photon absorption cross section when compared with simpler ketone derivatives. Due to strong polarization of the resulting dyes, values of two-photon absorption cross sections on the level of 200-300GM at 800nm were achieved, and thanks to that as well as the presence of the keto group, these new two-photon initiators display excellent performance so that the operating region is 5-75mW in some cases.

KW - Aldol reaction

KW - Ketones

KW - Photosensitizers

KW - Polymerization

KW - Two-photon absorption

UR - http://www.scopus.com/inward/record.url?scp=84920105777&partnerID=8YFLogxK

U2 - 10.1002/cphc.201402646

DO - 10.1002/cphc.201402646

M3 - Article

VL - 16

SP - 682

EP - 690

JO - ChemPhysChem

JF - ChemPhysChem

SN - 1439-4235

IS - 3

ER -