Piezochromic Luminescence Based on the Molecular Aggregation of 9,10‐Bis((E)‐2‐(pyrid‐2‐yl)vinyl)anthracene

Abstract

A chameleon under pressure: The observed piezochromic behavior of the title compound (BP2VA) was found to depend on its molecular aggregation state and specifically on the strength of the π–π interaction between the anthracene rings of adjacent molecules. When BP2VA is ground or placed under pressure, its molecular aggregation state changes, and a red shift in the fluorescence emission from green via orange to red occurs (see picture).

Molecular crystals based on 9,10-distyrylanthracene derivatives with high solid state fluorescence efficiency and uniaxial orientation induced by supramolecular interactions

“…Figure 1 shows the synthetic routes of CNDSA and t-BUDSA. As the intermediate products, compound (1) 9,10-bis(dichloromethyl)anthracene and compound (2) tetraethyl anthracene-9,10-diylbis(methylene)diphosphonate were synthesized according to the procedure reported [18].…”

Cation–Anion Interaction‐Directed Molecular Design Strategy for Mechanochromic Luminescence

“…It is worth noting that 1·NTf 2 is one of the smallest fl uorophore exhibiting an obvious mechanofl uorochromic behavior, which constitutes one of the longest emission wavelength redshifts reported so far. [ 2,14 ] …”

“…In particular, the number of mechanical-stimuli-responsive organic small molecule materials is still limited despite the popularity of organic fl uorophores. [ 1,2 ] Currently, mechanically induced luminescence changes have been observed mainly in certain metal (Au, Cu, Ag, Zn, Pt, Al, and Pd) [3][4][5][6][7][8][9] and boron complexes, [ 10 ] anthracene and pyrenebased molecules, [11][12][13][14] oligo( p -phenylene vinylene) derivatives, [ 15,16 ] and others. [17][18][19][20][21] Undoubtedly, it is highly desirable, yet very challenging, to establish fundamental principles of molecular design that can be applied to assemble a large number of libraries of mechanofl uorochromic dyes.…”

A stimuli-responsive double-stranded digold(i) helicate

“…[1][2][3][4][5] The subsequent reversion to their original luminescence colour is usually achieved upon recrystallization or thermal treatment. [1][2][3][4][5][9][10][11] These materials have attracted increased attention because of their potential 55 applications in optical storage and memories, mechanical sensors, displacement and deformation detectors, optoelectronic and display devices. 1 Such materials could also serve as models for studying the luminescent colour changes associated with structural changes of their molecular assemblies that switch from 60 one state to another under mechanical stimuli.…”