Publication detail

Four Slip-Stacked Arrangements, Three Types of Photophysics: Crystal Structure and Solid-State Fluorescence of 3,6-Diaryl Substituted Furo[3,4-c]furanone Polymorphs and Regioisomers

PAUK, K., LUŇÁK, S., MACHALICKÝ, O., PERDIH, F., VYŇUCHAL, J., ELIÁŠ, Z., IMRAMOVSKÝ, A.

Original Title

Four Slip-Stacked Arrangements, Three Types of Photophysics: Crystal Structure and Solid-State Fluorescence of 3,6-Diaryl Substituted Furo[3,4-c]furanone Polymorphs and Regioisomers

Type

journal article in Web of Science

Language

English

Original Abstract

Six symmetrical 3,6-diaryl (aryl=phenyl, 2-, 3- and 4-tolyl, 2,4- and 3,5-xylyl) substituted furo[3,4-c]furanones (DFF) were synthesized. The computational analysis, based on density functional theory, found eight possible centrosymmetrical slipped & pi;-stack arrangements, formed according to electron repulsion minimization principle, as for previously reported for & pi;-isoelectronic diketopyrrolopyrroles (DPP). One of these slipped stack arrangements was found to form infinite columns in the crystals of a new polymorph of parent phenyl derivative (with centre-to-centre distance CC=6.975 & ANGS;), other three types of stacks were found for 3-tolyl (CC=6.153 & ANGS;), 4-tolyl (CC=3.849 & ANGS;) and 2,4-xylyl (CC=4.856 & ANGS;) derivatives by single crystal X-ray diffractometry. All six derivatives show intense solution fluorescence in blue/green region, with a maximum driven entirely by a number and position of methyl substituents on phenyl rings. On the other hand, the solid-state fluorescence from yellow over orange to red is observed only for four derivatives and its presence/absence, spectral position and vibronic structure is driven exclusively by the slips in & pi;-stacks (with interplanar distance always less than 3.5 & ANGS;) of almost planar DFF molecules, resulting in J-type emission, H-type excimer-like emission and H-type quenching.

Keywords

fluorescence; density functional theory; furofuranones; diketopyrrolopyrroles; polymorphism; regioisomerism

Authors

PAUK, K., LUŇÁK, S., MACHALICKÝ, O., PERDIH, F., VYŇUCHAL, J., ELIÁŠ, Z., IMRAMOVSKÝ, A.

Released

23. 7. 2023

Publisher

WILEY-V C H VERLAG GMBH

Location

WEINHEIM

ISBN

2192-6506

Periodical

ChemPlusChem

Year of study

88

Number

8

State

Federal Republic of Germany

Pages count

15

URL

https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cplu.202300310

BibTex

@article{BUT187546,
  author="Stanislav {Luňák}",
  title="Four Slip-Stacked Arrangements, Three Types of Photophysics: Crystal Structure and Solid-State Fluorescence of 3,6-Diaryl Substituted Furo[3,4-c]furanone Polymorphs and Regioisomers",
  journal="ChemPlusChem",
  year="2023",
  volume="88",
  number="8",
  pages="15",
  doi="10.1002/cplu.202300310",
  issn="2192-6506",
  url="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cplu.202300310"
}