A1 Journal article (refereed)
From Terminal to Spiro‐Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes (2023)


Partanen, I., Belyaev, A., Su, B.-K., Liu, Z.-Y., Saarinen, J. J., Hashim Ishfaq, I., Steffen, A., Chou, P.-T., Romero-Nieto, C., & Koshevoy, I. O. (2023). From Terminal to Spiro‐Phosphonium Acceptors, Remarkable Moieties to Develop Polyaromatic NIR Dyes. Chemistry: A European Journal, 29(44), Article e202301073. https://doi.org/10.1002/chem.202301073


JYU authors or editors


Publication details

All authors or editorsPartanen, Iida; Belyaev, Andrey; Su, Bo-Kang; Liu, Zong-Ying; Saarinen, Jarkko J.; Hashim Ishfaq, Ibni; Steffen, Andreas; Chou, Pi-Tai; Romero-Nieto, Carlos; Koshevoy, Igor O.

Journal or seriesChemistry: A European Journal

ISSN0947-6539

eISSN1521-3765

Publication year2023

Publication date22/05/2023

Volume29

Issue number44

Article numbere202301073

PublisherWiley

Publication countryGermany

Publication languageEnglish

DOIhttps://doi.org/10.1002/chem.202301073

Publication open accessOpenly available

Publication channel open accessPartially open access channel

Publication is parallel published (JYX)https://jyx.jyu.fi/handle/123456789/89330


Abstract

Phosphonium-based compounds gain attention as a promising photofunctional materials. As a contribution to the emerging field, we present a series of donor-acceptor ionic dyes, which were constructed by tailoring the phosphonium (A) and extended π-NR2 (D) fragments to the anthracene framework. The alteration of the π-spacer of electron-donating substituents in species with terminal –+PPh2Me groups exhibits a long absorption wavelength up to λabs = 527 nm in dichloromethane and shifted the emission to the near-infrared (NIR) region (λ = 805 nm for thienyl aniline donor), although at low quantum yield (Φ < 0.01). In turn, the introduction of a P-heterocyclic acceptor substantially narrowed the optical bandgap and improved the efficiency of fluorescence. In particular, the phospha-spiro moiety allowed to attain NIR emission (797 nm in dichloromethane) with fluorescence efficiency of as high as Φ = 0.12. The electron-accepting property of phospha-spiro constituent outperformed that of the monocyclic and terminal phosphonium counterparts, illustrating a promising direction in the design of novel charge transfer chromophores.


Keywordsheterocyclic compoundsPAH compoundsphosphorusfluorescencephotochemistry

Free keywordsdonor-acceptor systems; fluorescence; phosphonium salt; phosphorus heterocycles; spiro compounds


Contributing organizations


Ministry reportingYes

Reporting Year2023

JUFO rating2


Last updated on 2024-15-05 at 13:12