Fluorescence sensor using porous host molecules deposited on filter paper with vapochromic and mechanochromic properties

Abstract

Naphthalenediimide derivative-absorbed papers, which were prepared by dropping chloroform solution, showed fluorescence under photoirradiation after exposure to vapors of small aromatic guests. The fluorescence intensity and maximum wavelength depended on...

Water Solubilization and Guest Molecule‐Induced Fluorescence Changes of Porous Host Molecules via Complexing with Polysaccharide or Polypeptide

“…[14] These results suggest that supramolecular host 2 dissociated into NDI and TPFB in water or on the paper. [14,19] In contrast, host 1 does not undergo dissociation because two bulky benzophenone moieties are connected via covalent bonding in 1. Herein, we describe the investigation of the I/I 0 values of 1-solubilizing agent complexes in comparison with those of 2-solubilizing agent complexes.…”

“…Recently, we reported that host molecules based on naphthalenediimide with bulky groups at both ends can include not only various small aromatic guest molecules but also generate fluorescence with a maximum emission wavelength at 400-500 nm depending on the type of guest molecules. [10][11][12][13][14][15] For example, N,N'-bis(2-aminobenzophenone)-1,4,5,8-naphthalenetetracarboxylic diimide (1) and N,N'-dipyrid-3-yl-1,4,5,8-naphthalenediimide (NDI) linked to two tris(pentafluorophenyl)borane (TPFB) molecules (2) formed a complex with small aromatic guest molecules such as benzene, toluene, and xylene in the solid state and on a filter paper (Figure 1). [10][11][12][13][14] Furthermore, we reported that a complex of 2 and poly-L-lysine (PLL) could be dissolved in an aqueous solution, [15] which is highly promising because the water solubilization of these functional host molecules is essential to widen their application scope.…”

“…[10][11][12][13][14][15] For example, N,N'-bis(2-aminobenzophenone)-1,4,5,8-naphthalenetetracarboxylic diimide (1) and N,N'-dipyrid-3-yl-1,4,5,8-naphthalenediimide (NDI) linked to two tris(pentafluorophenyl)borane (TPFB) molecules (2) formed a complex with small aromatic guest molecules such as benzene, toluene, and xylene in the solid state and on a filter paper (Figure 1). [10][11][12][13][14] Furthermore, we reported that a complex of 2 and poly-L-lysine (PLL) could be dissolved in an aqueous solution, [15] which is highly promising because the water solubilization of these functional host molecules is essential to widen their application scope. Since these materials belong to an interdisciplinary field between crystallography and supramolecular chemistry, we called them aqueous solutions with information on solids (ASIS).…”

Role of Halobenzene Guest Molecules in Modulating Room Temperature Phosphorescence of Benzophenone–Naphthalene Diimide Inclusion Crystals

“…In this study, we explore the creation of novel RTP materials using compound 1 , which consists of BP covalently linked with NDI (Figure 1(a)). Our group has previously demonstrated the versatility of compound 1 in forming inclusion crystals with various aromatic compounds, leading to applications in multi‐colored fluorescence, vapochromic, and piezochromic materials [33–37] . The exceptional guest inclusion ability of 1 is attributed to BP acting as a bulky substituent, providing nanospaces near NDI and thus facilitating the encapsulate ion of aromatic guest molecules.…”

“…Our group has previously demonstrated the versatility of compound 1 in forming inclusion crystals with various aromatic compounds, leading to applications in multi- colored fluorescence, vapochromic, and piezochromic materials. [33][34][35][36][37] The exceptional guest inclusion ability of 1 is attributed to BP acting as a bulky substituent, providing nanospaces near NDI and thus facilitating the encapsulate ion of aromatic guest molecules. Herein, we focused on creating inclusion crystals using compound 1 and halobenzenes such as chlorobenzene, bromobenzene, and iodobenzene.…”