Elsevier

Dyes and Pigments

Volume 186, February 2021, 109032
Dyes and Pigments

Review
Highly tunable aggregate-induced phosphorescence properties in persulfurated arenes

https://doi.org/10.1016/j.dyepig.2020.109032Get rights and content

Highlights

  • AIP feature of persulfurated arenes.

  • Tunable dual-emissive property.

  • Ways to control the dual-emissive nature.

Abstract

Persulfurated aromatic molecules, namely, persulfurated arenes, have been concerned in the field of organic synthesis, supramolecular chemistry, and electrocatalysis for decades. However, the luminescent properties of persulfurated arenes have long been underestimated. In recent years, follow-up observations reveal the mysterious shades of the aggregate-induced phosphorescence (AIP) feature of these compounds. Then, the AIP feature has received considerable attention afterwards. Till now, there is a growing trend of literatures that are dedicated to a further study of the AIP and a tunable fluorescence–phosphorescence complex emissive property of persulfurated arenes. Since this perspective is ignored in most other reviews in the relevant fields, herein, we aim to systematically review their development history of luminescent properties, shed light on their AIP and fluorescence–phosphorescence complex emissive property, and eventually try to conclude useful control ways to harness the attempting dual-emission nature.

Section snippets

History and overview

Persulfurated aromatic molecules, whose aromatic rings are persubstituted with sulfur ligands (Fig. 1), are intriguing both in chemical structure and in related properties [[1], [2], [3], [4], [5], [6], [7]]. Literatures mentioning synthesis routes of persulfurated aromatic molecules were frequently reported. In 1956, the first study of the "sulfhydryl" group in hexachlorobenzene and pyridine showed that the reaction was easy to occur [8]. In 1959, a paper entitled "Reaction of

Persulfurated arenes with the same substituents

In the long history of persulfurated arenes, the form of sodium thiophenol intermediates occupies a dominant position [26]. These intermediates can then undergo nucleophilic substitution reactions with polyfluorobenzene, polychlorobenzene or polybrominated benzene, etc. To generate the target products (Fig. 2) [[19], [20], [21],25,27].

However, at the beginning phase, the synthesis did not run smoothly, when two substrates were simply mixed in pyridine or ethanol. With this rough reaction

Aggregation-induce phosphorescence

Phosphorescence is always the desirable because of its unique photophysical processes and promising applications, such as sensors, bioimaging, photovoltaic devices, etc. [15] AIE materials are expected a rosy prospect on the fields of optical imaging [34], biological probes [35], cancer phototheranostics [36], etc. Fluorescence contributes greatly to the investigations of AIE materials. A new branch, aggregation-induced phosphorescence (AIP), however, has been paid less attention and greatly

Fluorescence–phosphorescence complex emission

Complex emission of phosphorescence and fluorescence in organic molecules was first reported by Fraser and coworkers, and soon became a burgeoning topic among the research community [40,44,45]. Behind the craze was their promising value among applications like smart materials [20], organic light-emitting diodes [46], safety protection [47] and etc. [27,48] Even though the complex emission owns such pleasant features mentioned above, the manipulation between fluorescence and phosphorescence

Summary

Even though solid history stands behind persulfurated arenes, they were delved very recently after discovering the aggregation-induced phosphorescence (AIP) property. Besides the rich history, design principles are key factors to understand the specialties and offer guidance into utilization. If synthesis is regarded as the beacon light, then special property of its derivatives is the central tower. Amazing feature of aggregation-induced phosphorescence broadens its applications. We here focus

Declaration of competing interest

The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.

Acknowledgements

This work was supported by 2019 NSFC (21975046), and partially by the National Key Research and Development Program of China (2017YFA0207700).

References (54)

  • S. Niembro et al.

    Star-shaped heavily fluorinated aromatic sulfurs: stabilization of palladium nanoparticles active as catalysts in cross-coupling reactions

    New J Chem

    (2008)
  • M. Villa et al.

    A turn-on phosphorescent sensor of Pb2+ in water by the formation of a coordination polymer

    Dalton Trans

    (2019)
  • A.L. Rocklin

    Substitution reactions of hexachlorobenzene

    J Org Chem

    (1956)
  • M. Kulka

    Reactions of hexachlorobenzene with mercaptides

    J Org Chem

    (1959)
  • W. Reifschneider

    Dow Chemicals Co. Chem. Abstr.

    (1964)
  • W. Reifschneider

    Dow Chemicals Co. Chem. Abstr.

    (1965)
  • W. Reifschneider

    Dow Chemicals Co. Chem. Abstr.

    (1967)
  • Spivack JD. DE 2819882....
  • Z. Zhao et al.

    Aggregation-induced emission: new vistas at the aggregate level

    Angew Chem Int Ed

    (2020)
  • J. Luo et al.

    Aggregation-induced emission of 1-methyl-1,2,3,4,5-pentaphenylsilole

    Chem Commun

    (2001)
  • D. Ding et al.

    Bioprobes based on AIE fluorogens

    Accounts of Chemical Research

    (2013)
  • W. Xi et al.

    Photophysical switching between aggregation-induced phosphorescence and dual-state emission by isomeric substitution

    Chem Eur J

    (2020)
  • X. Jia et al.

    Photoexcitation-controlled self-recoverable molecular aggregation for flicker phosphorescence

    Proc Natl Acad Sci Unit States Am

    (2019)
  • X. Jia et al.

    Fluorescence to multi-colored phosphorescence interconversion of a novel, asterisk-shaped luminogen via multiple external stimuli

    Chem Commun

    (2020)
  • H. Wu et al.

    Molecular stacking dependent phosphorescence–fluorescence dual emission in a single luminophore for self-recoverable mechanoconversion of multicolor luminescence

    Chem Commun

    (2017)
  • Y. Gong et al.

    Multiwavelength Anti-kasha’s rule emission on self-assembly of azulene-functionalized persulfurated arene

    J Phys Chem C

    (2019)
  • H. Wu et al.

    Crystal multi-conformational control through deformable carbon-sulfur bond for singlet-triplet emissive tuning

    Angew Chem Int Ed

    (2019)
  • Cited by (15)

    View all citing articles on Scopus
    View full text