Bistricyclic aromatic enes with fast conformational transition for ultrathin piezochromic films.

Chem Commun (Camb)

MOE Laboratory of Bioinorganic and Synthetic Chemistry, GBRCE for Functional Molecular Engineering, LIFM, IGCME, School of Chemistry, Sun Yat-Sen University, Guangzhou 510006, China.

Published: May 2025


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Article Abstract

New bistricyclic aromatic enes (BAEs) with a faster conformational transition were synthesized to improve the fabrication efficiency of BAE-based piezochromic films. Through ultrathin design, our 5-μm-thick BAE-based films can conform to non-planar surfaces and minimize disruption to the original interfacial pressure, improving the precision for mapping interfacial pressure distribution.

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http://dx.doi.org/10.1039/d5cc01054cDOI Listing

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New bistricyclic aromatic enes (BAEs) with a faster conformational transition were synthesized to improve the fabrication efficiency of BAE-based piezochromic films. Through ultrathin design, our 5-μm-thick BAE-based films can conform to non-planar surfaces and minimize disruption to the original interfacial pressure, improving the precision for mapping interfacial pressure distribution.

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Article Synopsis
  • New organic luminophores called bis(tricyclic) aromatic enes (BAEs), featuring 6-6-6-membered frameworks like acridine and xanthene, display blue-to-green fluorescence in solid states and polymer films with high quantum yields.
  • These BAEs are synthesized through a palladium-catalyzed double cross-coupling reaction, producing microcrystals or powders that fluoresce brilliantly.
  • Theoretical calculations indicate that their light absorption involves π-π* transitions, with a distinct charge transfer occurring in the 10,10-dioxido-9-thioxanthene variant.
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Fluorenylidene-xanthene and related polycyclic systems are typical examples of bistricyclic aromatic enes (BAEs); however, polycyclic systems of fluorenylidene-xanthene are relatively scarce. Here we synthesized a series of novel ladder-type polycyclic systems containing fluorenylidene-xanthene units, differing from the classic Barton's two-fold extrusion reaction. In the new synthetic scheme, the very popular Suzuki reaction was first used to couple the corresponding precursors, then a catalyst-free nucleophilic aromatic substitution reaction between Ar-F and Ar-OH groups in the backbone afforded ladder-type -heteroarenes.

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