Publication result detail

Versatile photoluminescence behavior of polycyclic hydroxybenzimidazoles driven by intermolecular hydrogen bonding

YORDANOV, D.; SMOLKA, R.; VALA, M.; WEITER, M.; GEORGIEV, A.

Original Title

Versatile photoluminescence behavior of polycyclic hydroxybenzimidazoles driven by intermolecular hydrogen bonding

English Title

Versatile photoluminescence behavior of polycyclic hydroxybenzimidazoles driven by intermolecular hydrogen bonding

Type

WoS Article

Original Abstract

Herein, the synthesis of polycyclic hydroxybenzimidazole based on 4-hydroxyphthalimide is presented and two isomeric structures are formed. The isomeric structures are capable of forming intermolecular hydrogen-bonded molecular associates. Hydroxybenzimidazole hydrogen-bonded organic frameworks have been shown to be sensitive to different solvent polarity, particularly in proton donor media, resulting in a blue shift in emission. The role of proton donor media has been evaluated using the binary mixture of acetonitrile/water and protonation by trifluoroacetic acid. The results show that by tuning the environment, the aggregation induced emission has appeared in the blue region and larger aggregates are formed compared to the less polar aprotic solvents. Under acidic conditions, the disruption of the hydrogen-bonded dimers was estimated, resulting in deep blue emission. This provides an opportunity to control the molecular associates and tune the optical behavior.

English abstract

Herein, the synthesis of polycyclic hydroxybenzimidazole based on 4-hydroxyphthalimide is presented and two isomeric structures are formed. The isomeric structures are capable of forming intermolecular hydrogen-bonded molecular associates. Hydroxybenzimidazole hydrogen-bonded organic frameworks have been shown to be sensitive to different solvent polarity, particularly in proton donor media, resulting in a blue shift in emission. The role of proton donor media has been evaluated using the binary mixture of acetonitrile/water and protonation by trifluoroacetic acid. The results show that by tuning the environment, the aggregation induced emission has appeared in the blue region and larger aggregates are formed compared to the less polar aprotic solvents. Under acidic conditions, the disruption of the hydrogen-bonded dimers was estimated, resulting in deep blue emission. This provides an opportunity to control the molecular associates and tune the optical behavior.

Keywords

Polycyclic benzimidazole; Non-covalent interactions; Hydrogen bonding; Photoluminescence; Organic frameworks

Key words in English

Polycyclic benzimidazole; Non-covalent interactions; Hydrogen bonding; Photoluminescence; Organic frameworks

Authors

YORDANOV, D.; SMOLKA, R.; VALA, M.; WEITER, M.; GEORGIEV, A.

RIV year

2025

Released

13.10.2024

Publisher

ELSEVIER

Location

AMSTERDAM

ISBN

0925-3467

Periodical

OPTICAL MATERIALS

Volume

157

Number

2

State

Kingdom of the Netherlands

Pages count

7

URL

https://www.sciencedirect.com/science/article/pii/S0925346724014575?via%3Dihub

BibTex

@article{BUT197039,
  author="YORDANOV, D. and SMOLKA, R. and VALA, M. and WEITER, M. and GEORGIEV, A.",
  title="Versatile photoluminescence behavior of polycyclic hydroxybenzimidazoles driven by intermolecular hydrogen bonding",
  journal="OPTICAL MATERIALS",
  year="2024",
  volume="157",
  number="2",
  pages="7",
  doi="10.1016/j.optmat.2024.116274",
  issn="0925-3467",
  url="https://www.sciencedirect.com/science/article/pii/S0925346724014575?via%3Dihub"
}