Tuning the aromatic backbone twist in dipyrrolonaphthyridinediones

Bartłomiej Sadowski; Dominik Mierzwa; Seongsoo Kang; Marek Grzybowski; Yevgen M. Poronik; Andrzej L. Sobolewski; Dongho Kim; Daniel T. Gryko

doi:10.1039/d1cc06863f

Tuning the aromatic backbone twist in dipyrrolonaphthyridinediones

Bartłomiej Sadowski, Dominik Mierzwa, Seongsoo Kang, Marek Grzybowski, Yevgen M. Poronik, Andrzej L. Sobolewski, Dongho Kim, Daniel T. Gryko

Department of Chemistry

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

Abstract

This communication describes the photophysical behavior of three analogs of cyclophane bearing the dipyrrolonaphthyridinedione (DPND) core. In these molecules, intersystem crossing (ISC) can be successfully induced by distinct changes in the deviation from planarity within the DPND core, allowing at the same time the emission maximum to shift from the green to red region of the visible spectrum without any synthetic modifications of the chromophore structure. This finding may build the foundation for a new paradigm for inducing ISC-type transitions within other centrosymmetric and planar cross-conjugated chromophores.

Original language	English
Pages (from-to)	3697-3700
Number of pages	4
Journal	Chemical Communications
Volume	58
Issue number	22
DOIs	https://doi.org/10.1039/d1cc06863f
Publication status	Published - 2022 Feb 21

Bibliographical note

Funding Information:
The work was financially supported by the Polish National Science Centre, Poland (HARMONIA 2016/22/M/ST5/00431 and SONATA 2018/31/D/ST5/00432) and the Foundation for Polish Science (TEAM POIR.04.04.00-00-3CF4/16-00). The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2021R1A2C3006308).

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Catalysis
Electronic, Optical and Magnetic Materials
Ceramics and Composites
Chemistry(all)
Surfaces, Coatings and Films
Metals and Alloys
Materials Chemistry

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10.1039/d1cc06863f

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title = "Tuning the aromatic backbone twist in dipyrrolonaphthyridinediones",

abstract = "This communication describes the photophysical behavior of three analogs of cyclophane bearing the dipyrrolonaphthyridinedione (DPND) core. In these molecules, intersystem crossing (ISC) can be successfully induced by distinct changes in the deviation from planarity within the DPND core, allowing at the same time the emission maximum to shift from the green to red region of the visible spectrum without any synthetic modifications of the chromophore structure. This finding may build the foundation for a new paradigm for inducing ISC-type transitions within other centrosymmetric and planar cross-conjugated chromophores.",

author = "Bart{\l}omiej Sadowski and Dominik Mierzwa and Seongsoo Kang and Marek Grzybowski and Poronik, {Yevgen M.} and Sobolewski, {Andrzej L.} and Dongho Kim and Gryko, {Daniel T.}",

note = "Funding Information: The work was financially supported by the Polish National Science Centre, Poland (HARMONIA 2016/22/M/ST5/00431 and SONATA 2018/31/D/ST5/00432) and the Foundation for Polish Science (TEAM POIR.04.04.00-00-3CF4/16-00). The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2021R1A2C3006308). Publisher Copyright: {\textcopyright} 2022 The Royal Society of Chemistry.",

year = "2022",

month = feb,

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doi = "10.1039/d1cc06863f",

language = "English",

volume = "58",

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AU - Sadowski, Bartłomiej

AU - Mierzwa, Dominik

AU - Kang, Seongsoo

AU - Grzybowski, Marek

AU - Poronik, Yevgen M.

AU - Sobolewski, Andrzej L.

AU - Kim, Dongho

AU - Gryko, Daniel T.

N1 - Funding Information: The work was financially supported by the Polish National Science Centre, Poland (HARMONIA 2016/22/M/ST5/00431 and SONATA 2018/31/D/ST5/00432) and the Foundation for Polish Science (TEAM POIR.04.04.00-00-3CF4/16-00). The work at Yonsei University was supported by the National Research Foundation of Korea (NRF) grant funded by the Korea government (MSIT) (No. 2021R1A2C3006308). Publisher Copyright: © 2022 The Royal Society of Chemistry.

PY - 2022/2/21

Y1 - 2022/2/21

N2 - This communication describes the photophysical behavior of three analogs of cyclophane bearing the dipyrrolonaphthyridinedione (DPND) core. In these molecules, intersystem crossing (ISC) can be successfully induced by distinct changes in the deviation from planarity within the DPND core, allowing at the same time the emission maximum to shift from the green to red region of the visible spectrum without any synthetic modifications of the chromophore structure. This finding may build the foundation for a new paradigm for inducing ISC-type transitions within other centrosymmetric and planar cross-conjugated chromophores.

AB - This communication describes the photophysical behavior of three analogs of cyclophane bearing the dipyrrolonaphthyridinedione (DPND) core. In these molecules, intersystem crossing (ISC) can be successfully induced by distinct changes in the deviation from planarity within the DPND core, allowing at the same time the emission maximum to shift from the green to red region of the visible spectrum without any synthetic modifications of the chromophore structure. This finding may build the foundation for a new paradigm for inducing ISC-type transitions within other centrosymmetric and planar cross-conjugated chromophores.

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ER -

Tuning the aromatic backbone twist in dipyrrolonaphthyridinediones

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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