Issue 32, 2022

Assembling photoactive materials from polycyclic aromatic hydrocarbons (PAHs): room temperature phosphorescence and excimer-emission in co-crystals with 1,4-diiodotetrafluorobenzene

Abstract

Co-crystallization between the polycyclic aromatic hydrocarbons anthracene (A) and 9-methylanthracene (MA) with 1,4-diiodotetrafluorobenzene (I2F4) afforded three novel co-crystals, viz. A·(I2F4)2 and an unexpectedly complex system with two distinct compositions, namely MA·I2F4 and (MA)4·I2F4, which can be mechanochemically interconverted by a change in the stoichiometry of the reactive mixtures. Interestingly, all co-crystals are dual-emissive materials and exhibit different mechanisms of emission. A·(I2F4)2 and MA·I2F4 fluoresce from isolated molecules, whereas the luminescence of (MA)4·I2F4 is dominated by excimer emission. In all cases, phosphorescence at RT (RTP) is observed and interpreted as a direct consequence of the interactions between the iodine atoms of the I2F4 co-former and the π-electron density of the anthracene aromatic rings. Furthermore, [4 + 4] photoactivity within (MA)4·I2F4 was also investigated by means of FTIR/NMR spectroscopy and PXRD. The photophysical and photochemical behaviors of all solids are discussed and rationalized based on their structural features.

Graphical abstract: Assembling photoactive materials from polycyclic aromatic hydrocarbons (PAHs): room temperature phosphorescence and excimer-emission in co-crystals with 1,4-diiodotetrafluorobenzene

Supplementary files

Article information

Article type
Paper
Submitted
24 May 2022
Accepted
14 Jul 2022
First published
15 Jul 2022
This article is Open Access
Creative Commons BY-NC license

CrystEngComm, 2022,24, 5748-5756

Assembling photoactive materials from polycyclic aromatic hydrocarbons (PAHs): room temperature phosphorescence and excimer-emission in co-crystals with 1,4-diiodotetrafluorobenzene

A. Azzali, S. d'Agostino, M. Capacci, F. Spinelli, B. Ventura and F. Grepioni, CrystEngComm, 2022, 24, 5748 DOI: 10.1039/D2CE00720G

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