Publication detail

Fluorescent Rotary Switches: Four- vs Three-Substituted Phthalimide Boron Difluoride Schiff Base Complexes

YORDANOV, D. SMOLKA, R. NAKASHIMA, K. HIRASHIMA, S. MATSUSHIMA, Y. VALA, M. KRAJČOVIČ, J. WEITER, M. MIURA, T. GEORGIEV, A.

Original Title

Fluorescent Rotary Switches: Four- vs Three-Substituted Phthalimide Boron Difluoride Schiff Base Complexes

Type

journal article in Web of Science

Language

English

Original Abstract

The influence of the substitution pattern in phthalimide boron difluoride Schiff base complexes as fluorescent molecular rotors has been investigated. Due to their ground-state zwitterionic structures, they have exhibited negative solvatochromism in absorption and blue-green emission with moderate to satisfactory photoluminescence quantum yields in solution. Ground-state and excited-state theoretical calculations and time-resolved emission spectroscopy revealed that the excited-state rotation is triggered by planar-induced charge transfer, resulting in switched emission toward the green region. Fluorescence lifetime measurements and species-associated emission spectra exhibited two emitting excited species in equilibrium via a planar transition-state barrier. The substitution pattern models showed different behavior in solid-state mechanochromic switching and were analyzed by subcell unit packing obtained from X-ray structure data. We have attempted to gain in-depth insight into the fluorescence mechanism and photoluminescence properties associated with the substitution pattern of the phthalimide motif in order to understand the structure-property-function relationship.

Keywords

Phthalimide; Photoluminescence; Molecular rotors; Fluorescence rotary switches; Twisting intramolecular charge transfer; Planar-induced charge transfer; Mechanochromic switching

Authors

YORDANOV, D.; SMOLKA, R.; NAKASHIMA, K.; HIRASHIMA, S.; MATSUSHIMA, Y.; VALA, M.; KRAJČOVIČ, J.; WEITER, M.; MIURA, T.; GEORGIEV, A.

Released

21. 11. 2023

Publisher

AMER CHEMICAL SOC

Location

WASHINGTON

ISBN

0022-3263

Periodical

JOURNAL OF ORGANIC CHEMISTRY

Year of study

88

Number

24

State

United States of America

Pages from

17206

Pages to

17214

Pages count

9

URL

https://pubs.acs.org/doi/full/10.1021/acs.joc.3c02056

BibTex

@article{BUT187806,
  author="YORDANOV, D. and SMOLKA, R. and NAKASHIMA, K. and HIRASHIMA, S. and MATSUSHIMA, Y. and VALA, M. and KRAJČOVIČ, J. and WEITER, M. and MIURA, T. and GEORGIEV, A.",
  title="Fluorescent Rotary Switches: Four- vs Three-Substituted Phthalimide Boron Difluoride Schiff Base Complexes",
  journal="JOURNAL OF ORGANIC CHEMISTRY",
  year="2023",
  volume="88",
  number="24",
  pages="17206--17214",
  doi="10.1021/acs.joc.3c02056",
  issn="0022-3263",
  url="https://pubs.acs.org/doi/full/10.1021/acs.joc.3c02056"
}