Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes

Krzysztof Bartkowski; Abhishek Kumar Gupta; Tomas Matulaitis; Maja Morawiak; Eli Zysman-Colman; Marcin Lindner

doi:10.1039/d3qo01914d

Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes

Krzysztof Bartkowski, Abhishek Kumar Gupta, Tomas Matulaitis, Maja Morawiak, Eli Zysman-Colman^*, Marcin Lindner^*

^*Corresponding author for this work

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

Abstract

We report the synthesis and characterization of the first pyrrolizine-embedded PAH systems. The bipolar core, based on a naphthalimide and indole fusion, was successfully synthesized through a one-pot cascade of Suzuki/Boc deprotection/Buchwald–Hartwig transformations. A facile post-functionalization of the unoccupied β-position of the heterocycle with aromatic amines as donor subunits led to a set of donor–acceptor architecture-based dyes. Effective narrowing of the HOMO–LUMO gap, along with its tuning by changing donor strength together with stabilization of π conjugation within the pyrrolizine–NMI core, provided a route to near-infrared (NIR) emission not only in solution (∼740 nm) but also in the solid-state (∼700 nm).

Original language	English
Pages (from-to)	755-760
Number of pages	6
Journal	Organic Chemistry Frontiers
Volume	11
Issue number	3
Early online date	4 Dec 2023
DOIs	https://doi.org/10.1039/d3qo01914d
Publication status	Published - 7 Feb 2024

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Bartkowski_2023_OCF_Pyrrolizine-fused_CCBYY
Copyright © 2023 The Authors. Open Access. This article is licensed under a Creative Commons Attribution 3.0 Unported Licence.
Final published version, 1.67 MBLicence: CC BY

Cite this

@article{f3723c82ede64cd59f64f0c31a2d7941,

title = "Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes",

abstract = "We report the synthesis and characterization of the first pyrrolizine-embedded PAH systems. The bipolar core, based on a naphthalimide and indole fusion, was successfully synthesized through a one-pot cascade of Suzuki/Boc deprotection/Buchwald–Hartwig transformations. A facile post-functionalization of the unoccupied β-position of the heterocycle with aromatic amines as donor subunits led to a set of donor–acceptor architecture-based dyes. Effective narrowing of the HOMO–LUMO gap, along with its tuning by changing donor strength together with stabilization of π conjugation within the pyrrolizine–NMI core, provided a route to near-infrared (NIR) emission not only in solution (∼740 nm) but also in the solid-state (∼700 nm).",

author = "Krzysztof Bartkowski and Gupta, \{Abhishek Kumar\} and Tomas Matulaitis and Maja Morawiak and Eli Zysman-Colman and Marcin Lindner",

note = "K. B. and M. L. acknowledge support from the National Centre for Research and Development, Poland, Grant No. LIDER/21/0077/L-11/19/NCBR/2020. M. L. is a recipient of a scholarship awarded by the Polish Ministry of Education and Science to outstanding young scientists (2/DSP/2021). The St Andrews team thanks the Leverhulme Trust (RPG-2022-032) and the Engineering and Physical Sciences Research Council (EP/R035164/1, EP/W007517) for support.",

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doi = "10.1039/d3qo01914d",

language = "English",

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journal = "Organic Chemistry Frontiers",

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T1 - Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes

AU - Bartkowski, Krzysztof

AU - Gupta, Abhishek Kumar

AU - Matulaitis, Tomas

AU - Morawiak, Maja

AU - Zysman-Colman, Eli

AU - Lindner, Marcin

N1 - K. B. and M. L. acknowledge support from the National Centre for Research and Development, Poland, Grant No. LIDER/21/0077/L-11/19/NCBR/2020. M. L. is a recipient of a scholarship awarded by the Polish Ministry of Education and Science to outstanding young scientists (2/DSP/2021). The St Andrews team thanks the Leverhulme Trust (RPG-2022-032) and the Engineering and Physical Sciences Research Council (EP/R035164/1, EP/W007517) for support.

PY - 2024/2/7

Y1 - 2024/2/7

N2 - We report the synthesis and characterization of the first pyrrolizine-embedded PAH systems. The bipolar core, based on a naphthalimide and indole fusion, was successfully synthesized through a one-pot cascade of Suzuki/Boc deprotection/Buchwald–Hartwig transformations. A facile post-functionalization of the unoccupied β-position of the heterocycle with aromatic amines as donor subunits led to a set of donor–acceptor architecture-based dyes. Effective narrowing of the HOMO–LUMO gap, along with its tuning by changing donor strength together with stabilization of π conjugation within the pyrrolizine–NMI core, provided a route to near-infrared (NIR) emission not only in solution (∼740 nm) but also in the solid-state (∼700 nm).

AB - We report the synthesis and characterization of the first pyrrolizine-embedded PAH systems. The bipolar core, based on a naphthalimide and indole fusion, was successfully synthesized through a one-pot cascade of Suzuki/Boc deprotection/Buchwald–Hartwig transformations. A facile post-functionalization of the unoccupied β-position of the heterocycle with aromatic amines as donor subunits led to a set of donor–acceptor architecture-based dyes. Effective narrowing of the HOMO–LUMO gap, along with its tuning by changing donor strength together with stabilization of π conjugation within the pyrrolizine–NMI core, provided a route to near-infrared (NIR) emission not only in solution (∼740 nm) but also in the solid-state (∼700 nm).

UR - https://www.scopus.com/pages/publications/85179806361

U2 - 10.1039/d3qo01914d

DO - 10.1039/d3qo01914d

M3 - Article

SN - 2052-4129

VL - 11

SP - 755

EP - 760

JO - Organic Chemistry Frontiers

JF - Organic Chemistry Frontiers

IS - 3

ER -

Using pyrrolizine-fused bipolar PAHs as a new strategy towards efficient red and NIR emissive dyes

Abstract

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