Side Chain Regioisomers that Dictate Optical Properties and Mechanofluorochromism through Crystal Packing

Sharber, Seth A.; Thomas III, Samuel W.

doi:10.1021/acs.chemmater.0c01676

Side Chain Regioisomers that Dictate Optical Properties and Mechanofluorochromism through Crystal Packing

Journal Article · Mon May 18 00:00:00 EDT 2020 · Chemistry of Materials

DOI:https://doi.org/10.1021/acs.chemmater.0c01676· OSTI ID:1656806

Sharber, Seth A. ^[1]; ^[2]

Tufts Univ., Medford, MA (United States); Aramco Services Company, Cambridge, MA (United States); Tufts University
Tufts Univ., Medford, MA (United States)

Designing strong interactions into $$π$$-conjugated materials can direct their typically uncontrolled molecular packing and is an important strategy toward tuning their technologically relevant properties in the solid state. In this paper we demonstrate unconventional control over solid-state fluorescence and mechanofluorochromism (MFC) through regiochemical substitutions in side chains of 12 three-ring phenylene ethynylenes (PEs) that employ fluoroarene–arene (ArF–ArH) interactions between tetrafluoro ArF pendants and PE main chains to direct crystal packing, with single-atom variations of the lone proton in ArF pendants between 4-hydro, 5-hydro, and 6-hydro substitution yielding in two cases dramatically different fluorescence and MFC behavior. X-ray crystal structures reveal key intermolecular interactions of ArF rings, including their lone protons, which vary as a function of substitution pattern and contribute to optical properties in solids. Rarely reported, particularly with such dramatic results, this systematic study on regiochemical effects over solid-state properties demonstrates the versatility of using discrete, directional interactions of side chains for noncovalent control in conjugated materials.

View Accepted Manuscript (DOE)

Research Organization:: Tufts Univ., Medford, MA (United States)

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0016423

OSTI ID:: 1656806

Journal Information:: Chemistry of Materials, Journal Name: Chemistry of Materials Journal Issue: 13 Vol. 32; ISSN 0897-4756

Publisher:: American Chemical Society (ACS)Copyright Statement

Country of Publication:: United States

Language:: English

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Side Chain Regioisomers that Dictate Optical Properties and Mechanofluorochromism through Crystal Packing

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