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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
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" }