Exploration of the Luminescence Properties of Organic Phosphate Salts of 3‐Quinoline‐ and 5‐Isoquinolineboronic Acid

Abstract

3-Quinoline-and 5-isoquinolineboronic acids (3QBA and 5IQBA) were combined with 1-naphthyl and diphenyl phosphate (1NP and DPP) to give three crystalline molecular salts of 1:1 stoichiometric composition, viz., 3QBA-1NP, 5IQBA-1NP and 3QBA-DPP. The products were characterized by elemental analysis, single-crystal X-ray diffraction studies, IR spectroscopy, luminescence spectroscopy and TG-DSC measurements. The analysis of the solid-state structures revealed that the molecular components are linked by strong charge-assisted hydrogen bonds forming heterodimeric synthons of the type B(OH) 2 ··· -O 2 P and N + -H···O(P). In addition, the hydrogen phos- [a] Crystalline solids of compounds 3QBA-1NP, 5IQBA-1NP and 3QBA-DPP were isolated upon combination of the starting reagents in absolute ethanol. The products were characterized by elemental analysis, single-crystal X-ray diffraction (SCXRD) analysis, IR spectroscopy and TG-DSC analysis. In addition, the luminescence properties were explored. 2708 Scheme 1. List of compounds employed for the formation of the molecular salts described in this contribution.

Channel Confinement of Aromatic Petrochemicals via Aryl–Perfluoroaryl Interactions With a B←N Host

“…In this context, an emerging solid-state ordering strategy relies on the use of boronic acids and derivatives to confine guests into a crystal lattice (Nishiyabu et al, 2011; Bull et al, 2013). The inclusion properties are facilitated by multiple supramolecular interactions of boronic acids and derivatives (e.g., hydrogen bonding (Campillo-Alvarado et al, 2018a,b; Ruelas-Alvarez et al, 2019), reversible esterification Fornasari et al, 2019; Takahashi et al, 2019, π-π interactions and B←N coordination Campillo-Alvarado et al, 2019; Ono and Hisaeda, 2019; Stephens et al, 2019).…”

Systematic arrangement control of functional organic molecules

“…Functional organic molecules with tunable properties are composed of earth-abundant and readily available building blocks (C, H, O, N, and S). 1 One of the typical examples is π-conjugated molecules, which exhibit luminescence and conductivity owing to their interaction with light [2][3][4][5][6][7][8] and their electron transport capabilities, [9][10][11][12][13][14][15][16] respectively. As a result, they are expected to play an important role in a variety of research fields, including electroluminescence, 2,6-8 photovoltaics, 9,10 electronics, 11 and energy production and storage.…”

“…1 One of the typical examples is π-conjugated molecules, which exhibit luminescence and conductivity owing to their interaction with light 2–8 and their electron transport capabilities, 9–16 respectively. As a result, they are expected to play an important role in a variety of research fields, including electroluminescence, 2,6–8 photovoltaics, 9,10 electronics, 11 and energy production and storage. 12 Since these properties of π-conjugated molecules are strongly influenced by the overlap of π-orbitals between adjacent molecules in the solid-state and the spread of π-conjugation within a molecule, their molecular arrangements as well as their molecular structures have been recognized as critical.…”

The influence of chalcogen atom on conformation and phase transition in chalcogenazinoquinolinium monoiodides

“…Moreover, quinolinium derivatives are widely employed as effective synthons in the design of biologically active compounds, for example, as anticancer and antibacterial agents (Jin et al, 2020). Luminescence of metalfree quinolinium derivatives, including co-crystals, polymers and salts, has been intensively studied in recent years (Ruelas-ISSN 2052-5206 Alvarez et al, 2019;Kaya et al, 2018;Bai et al, 2017). Optical properties of quinoline and isoquinoline in the context of hydrogen bonding have also been described earlier (Anton & Moomaw, 1977).…”