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

Result code in IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00216305%3A26310%2F23%3APU150520" target="_blank" >RIV/00216305:26310/23:PU150520 - isvavai.cz</a>

Result on the web

<a href="https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cplu.202300310" target="_blank" >https://chemistry-europe.onlinelibrary.wiley.com/doi/full/10.1002/cplu.202300310</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1002/cplu.202300310" target="_blank" >10.1002/cplu.202300310</a>

Result language

angličtina

Original language name

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

Original language description

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.

Czech name

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Czech description

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Type

J_imp - Article in a specialist periodical, which is included in the Web of Science database

CEP classification

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OECD FORD branch

10400 - Chemical sciences

Project

<a href="/en/project/GA19-22783S" target="_blank" >GA19-22783S: Molecular energy harvesting materials: towards breaking the limits</a><br>

Continuities

P - Projekt vyzkumu a vyvoje financovany z verejnych zdroju (s odkazem do CEP)

Publication year

2023

Confidentiality

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Name of the periodical

ChemPlusChem

ISSN

2192-6506

e-ISSN

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Volume of the periodical

88

Issue of the periodical within the volume

8

Country of publishing house

DE - GERMANY

Number of pages

15

Pages from-to

„“-„“

UT code for WoS article

001044166800001

EID of the result in the Scopus database

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