Application of Rigidity‐Controlled Supramolecular Affinity Materials for the Gravimetric Detection of Hazardous and Illicit Compounds

Abstract

The combination of an (−)‐isosteviol‐derived building block and 9,9’‐spirobifluorene or tetraphenylmethane generated highly potent new affinity materials for the detection of volatile organic compounds (VOCs). Comparison of their affinity behaviour with different core structures showed remarkable influence on selectivity and sensitivity due to structural rigidity and their pre‐organization. Their unique supramolecular properties were investigated in an affinity assay using high fundamental frequency quartz crystal microbalances.

Synthesis of 9,9′‐Spirobifluorenes and 4,5‐Diaza‐9,9′‐spirobifluorenes and Their Application as Affinity Materials for Quartz Crystal Microbalances

“…The advantages of HFF-QCMs are the improved lower detection limit and the faster response time, compared with normalQ CMs (5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18)(19)(20). This study displays the unique interactions of these materials with volatile organicc ompounds( VOCs) in the vapor phase.…”

“…[7] Moreover, the design of functional groups that enable hydrogen [14b] or halogen bonding [29] favor the specific affinity towards ad esired analyte. [7] Moreover, the design of functional groups that enable hydrogen [14b] or halogen bonding [29] favor the specific affinity towards ad esired analyte.…”

“…[2][3][4][5][6][7][8][9]trifluoromethansulfonate (3), [15] 2-bromo-5-(trimethylsilyl)pyridine (6), [18] 5,5'-bis(trimethylsilyl)-2,2'-bipyridine (7), [19] 2,2'bis(4,4,5,5-tetramethyl-1,2,3-dioxaborolan-2-yl)-9,9'-spirobifluorene ((R)-9), [20a] 2-bromo-5-hydroxypyridine (11), [21] 2-bromo-5-methoxypyridine (12), [21] 4,5-diazafluoren-9-one (17), [23,24] 4,5-diazafluoren-9-(2-biphenyl)ol (18), [26] 4, 5-diaza-9,9'-spirobifluorene (19), [25] 2',7'-dibromo-4,5-diaza-9,9'-spirobifluorene (14), [25] 2-bromo-(22)a nd 2methoxynicotinic acid methyl ester (23), [26] and 2-iodobiphenyl [24] were prepared according to protocols reported in the literature. TLC was performed on aluminum TLC plates (silica gel 60F 254 from Merck).…”

“…[5] Rigid dendrimers, such as dendritic polyphenylenes, have also proven to be excellent affinity materials for applications in QCMs. [7] However,i ts hould be noted that these features are also required for ab road range of other applications of this particular class of compounds, [8] including molecular recognition, [9] catalysis, [10] coordination chemistry, [11] macromolecular chemistry, [12] and optoelectronics. [7] However,i ts hould be noted that these features are also required for ab road range of other applications of this particular class of compounds, [8] including molecular recognition, [9] catalysis, [10] coordination chemistry, [11] macromolecular chemistry, [12] and optoelectronics.…”

“…[7] However,i ts hould be noted that these features are also required for ab road range of other applications of this particular class of compounds, [8] including molecular recognition, [9] catalysis, [10] coordination chemistry, [11] macromolecular chemistry, [12] and optoelectronics. [7,14] [7,14] …”