Tuning the Emission Behaviour of Halogenated Bridged Ethers in Solution, as Solids and as Aggregates by Chalcogen Substitution

Justin Dubbert; Marco Valtolina; Alexander Huber; Tim D. Scherz; Christoph Wölper; Constantin G. Daniliuc; Ofer Filiba; Saumik Sen; Igor Schapiro; Fabio Rizzo; Jens Voskuhl

doi:10.1002/cptc.202200169

Tuning the Emission Behaviour of Halogenated Bridged Ethers in Solution, as Solids and as Aggregates by Chalcogen Substitution

Justin Dubbert, Marco Valtolina, Alexander Huber, Tim D. Scherz, Christoph Wölper, Constantin G. Daniliuc, Ofer Filiba, Saumik Sen, Igor Schapiro, Fabio Rizzo^*, Jens Voskuhl^*

^*Corresponding author for this work

Institute of Chemistry

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

2 Scopus citations

Abstract

In this contribution, we describe a set of three chlorinated bridged ethers with varying numbers of sulfur and oxygen atoms. The substitution leads to highly emissive compounds with tunable photophysical properties in relationship to their state of aggregation, i. e. in solution, as aggregates and in the solid state. Additionally, an in-depth X-ray diffractometric analysis supported by a Hirshfeld study of non-covalent interactions and quantum chemical simulations was carried out. As the outcome, it was found that the content of sulfur in the compounds regulates the tuning of emission in solution as well as in the aggregated states as a consequence of their variation of planarity.

Original language	American English
Article number	e202200169
Journal	ChemPhotoChem
Volume	7
Issue number	1
DOIs	https://doi.org/10.1002/cptc.202200169
State	Published - Jan 2023

Bibliographical note

Funding Information:
JV, JD and FR thank the Deutsche Forschungsgemeinschaft (DFG) – (Grant: VO 2383/1-1, project number: 405679982, to JV, RI 2635/6-1, project number: 464509280 to FR) for funding. I.S. and O.F. acknowledge funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – Project-ID 221545957 – SFB 1078/C6. Additionally Steffen Riebe and Harini Hemesh are acknowledged for experiments conducted in the initial phase of the project and growing of the single crystals. We thank the Center for Nanointegration Duisburg-Essen (CENIDE) for financial support. Open Access funding enabled and organized by Projekt DEAL.

Funding Information:
JV, JD and FR thank the Deutsche Forschungsgemeinschaft (DFG) – (Grant: VO 2383/1‐1, project number: 405679982, to JV, RI 2635/6‐1, project number: 464509280 to FR) for funding. I.S. and O.F. acknowledge funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – Project‐ID 221545957 – SFB 1078/C6. Additionally Steffen Riebe and Harini Hemesh are acknowledged for experiments conducted in the initial phase of the project and growing of the single crystals. We thank the Center for Nanointegration Duisburg‐Essen (CENIDE) for financial support. Open Access funding enabled and organized by Projekt DEAL.

Publisher Copyright:
© 2022 The Authors. ChemPhotoChem published by Wiley-VCH GmbH.

Keywords

aggregation
aggregation-induced emission
chalcogens
computational chemistry
solid-state structures

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10.1002/cptc.202200169

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title = "Tuning the Emission Behaviour of Halogenated Bridged Ethers in Solution, as Solids and as Aggregates by Chalcogen Substitution",

abstract = "In this contribution, we describe a set of three chlorinated bridged ethers with varying numbers of sulfur and oxygen atoms. The substitution leads to highly emissive compounds with tunable photophysical properties in relationship to their state of aggregation, i. e. in solution, as aggregates and in the solid state. Additionally, an in-depth X-ray diffractometric analysis supported by a Hirshfeld study of non-covalent interactions and quantum chemical simulations was carried out. As the outcome, it was found that the content of sulfur in the compounds regulates the tuning of emission in solution as well as in the aggregated states as a consequence of their variation of planarity.",

keywords = "aggregation, aggregation-induced emission, chalcogens, computational chemistry, solid-state structures",

author = "Justin Dubbert and Marco Valtolina and Alexander Huber and Scherz, {Tim D.} and Christoph W{\"o}lper and Daniliuc, {Constantin G.} and Ofer Filiba and Saumik Sen and Igor Schapiro and Fabio Rizzo and Jens Voskuhl",

note = "Funding Information: JV, JD and FR thank the Deutsche Forschungsgemeinschaft (DFG) – (Grant: VO 2383/1-1, project number: 405679982, to JV, RI 2635/6-1, project number: 464509280 to FR) for funding. I.S. and O.F. acknowledge funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – Project-ID 221545957 – SFB 1078/C6. Additionally Steffen Riebe and Harini Hemesh are acknowledged for experiments conducted in the initial phase of the project and growing of the single crystals. We thank the Center for Nanointegration Duisburg-Essen (CENIDE) for financial support. Open Access funding enabled and organized by Projekt DEAL. Funding Information: JV, JD and FR thank the Deutsche Forschungsgemeinschaft (DFG) – (Grant: VO 2383/1‐1, project number: 405679982, to JV, RI 2635/6‐1, project number: 464509280 to FR) for funding. I.S. and O.F. acknowledge funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – Project‐ID 221545957 – SFB 1078/C6. Additionally Steffen Riebe and Harini Hemesh are acknowledged for experiments conducted in the initial phase of the project and growing of the single crystals. We thank the Center for Nanointegration Duisburg‐Essen (CENIDE) for financial support. Open Access funding enabled and organized by Projekt DEAL. Publisher Copyright: {\textcopyright} 2022 The Authors. ChemPhotoChem published by Wiley-VCH GmbH.",

year = "2023",

month = jan,

doi = "10.1002/cptc.202200169",

language = "American English",

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AU - Dubbert, Justin

AU - Valtolina, Marco

AU - Huber, Alexander

AU - Scherz, Tim D.

AU - Wölper, Christoph

AU - Daniliuc, Constantin G.

AU - Filiba, Ofer

AU - Sen, Saumik

AU - Schapiro, Igor

AU - Rizzo, Fabio

AU - Voskuhl, Jens

N1 - Funding Information: JV, JD and FR thank the Deutsche Forschungsgemeinschaft (DFG) – (Grant: VO 2383/1-1, project number: 405679982, to JV, RI 2635/6-1, project number: 464509280 to FR) for funding. I.S. and O.F. acknowledge funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – Project-ID 221545957 – SFB 1078/C6. Additionally Steffen Riebe and Harini Hemesh are acknowledged for experiments conducted in the initial phase of the project and growing of the single crystals. We thank the Center for Nanointegration Duisburg-Essen (CENIDE) for financial support. Open Access funding enabled and organized by Projekt DEAL. Funding Information: JV, JD and FR thank the Deutsche Forschungsgemeinschaft (DFG) – (Grant: VO 2383/1‐1, project number: 405679982, to JV, RI 2635/6‐1, project number: 464509280 to FR) for funding. I.S. and O.F. acknowledge funding by the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – Project‐ID 221545957 – SFB 1078/C6. Additionally Steffen Riebe and Harini Hemesh are acknowledged for experiments conducted in the initial phase of the project and growing of the single crystals. We thank the Center for Nanointegration Duisburg‐Essen (CENIDE) for financial support. Open Access funding enabled and organized by Projekt DEAL. Publisher Copyright: © 2022 The Authors. ChemPhotoChem published by Wiley-VCH GmbH.

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N2 - In this contribution, we describe a set of three chlorinated bridged ethers with varying numbers of sulfur and oxygen atoms. The substitution leads to highly emissive compounds with tunable photophysical properties in relationship to their state of aggregation, i. e. in solution, as aggregates and in the solid state. Additionally, an in-depth X-ray diffractometric analysis supported by a Hirshfeld study of non-covalent interactions and quantum chemical simulations was carried out. As the outcome, it was found that the content of sulfur in the compounds regulates the tuning of emission in solution as well as in the aggregated states as a consequence of their variation of planarity.

AB - In this contribution, we describe a set of three chlorinated bridged ethers with varying numbers of sulfur and oxygen atoms. The substitution leads to highly emissive compounds with tunable photophysical properties in relationship to their state of aggregation, i. e. in solution, as aggregates and in the solid state. Additionally, an in-depth X-ray diffractometric analysis supported by a Hirshfeld study of non-covalent interactions and quantum chemical simulations was carried out. As the outcome, it was found that the content of sulfur in the compounds regulates the tuning of emission in solution as well as in the aggregated states as a consequence of their variation of planarity.

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KW - aggregation-induced emission

KW - chalcogens

KW - computational chemistry

KW - solid-state structures

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JO - ChemPhotoChem

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ER -

Tuning the Emission Behaviour of Halogenated Bridged Ethers in Solution, as Solids and as Aggregates by Chalcogen Substitution

Abstract

Bibliographical note

Keywords

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