Synthesis of functionalized 1,2-diphenylacetylene derivatives

A new chiral hydrogen-bonded organic framework (HOF) ZIOC-2 was synthesized using an optically active building block, namely, L-prolineamide-substituted diarylacetylenedicarboxylic acid (4,4′-ethyne-1,2-diyl-bis[3-(L-prolylamino) benzoic acid], EDPABA). Self-assembly of EDPABA in aqueous medium results in the crystallization of either sesquihydrate ZIOC-2 1.5H 2 O or tetrahydrate ZIOC-2 4H 2 O. The latter tetrahydrate form can be irreversibly transformed into the sesquihydrate one under heating up to 35 °C. The full dehydration of the sesquihydrate form occurs at 150 °C in open air and at 220 °C, when the sample was placed into a sealed capillary. The anhydrous crystalline form, denoted as ZIOC-2, remains intact upon heating up to 225 °C. Crystal structures of the synthesized novel materials were established with the use of X-ray powder diffraction data. The structural examinations have shown that the ZIOC-2 framework can reversibly absorb and desorb water molecules. The potential application field of the novel HOF material can be related to the absorption from liquid and gas phases.

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“…The new homochiral diarylacetylene 2 was synthesized based on a previously developed methodology. 13,23 In this way, S8).…”

Section: ■ Results and Discussionmentioning

confidence: 97%

Synthesis and Crystal Structure of a New Chiral Hydrogen-Bonded Organic Framework ZIOC-2

Veselovsky

Исаева

Kustov

et al. 2022

Crystal Growth & Design

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“…TMSCl (2.12 g, 19.56 mmol) was added to a solution of diarylacetylene 2 (0.75 g, 1.08 mmol) in 30 mL of MeOH stirred at 20 °C under argon. The reaction was stirred additionally for 5 h and kept overnight.…”

Section: Methodsmentioning

confidence: 99%

“…Taking into account the considerations mentioned above, we aimed to construct a chiral HOF by the use as an optically active building block, i.e., diarylacetylene dicarboxylic acid modified by the l -prolineamide moiety at both aromatic rings. The building block 3,3′-ethyne-1,2-diylbis[6-( l -prolylamino)benzoic acid] (EDPBA, 1 ) was synthesized from precursor dimethyl 3,3′-ethyne-1,2-diylbis[6-( N - tert -butoxycarbonyl- l -prolylamino)benzoic acid] ( 2 ) reported by us previously . Self-assembly under appropriate conditions led to formation a new hydrogen-bonded framework denoted as ZIOC-1 .…”

Section: Introductionmentioning

confidence: 99%

“…The building block 3,3′-ethyne-1,2-diylbis[6-(L-prolylamino)benzoic acid] (EDPBA, 1) was synthesized from precursor dimethyl 3,3′-ethyne-1,2-diylbis[6-(N-tert-butoxycarbonyl-Lprolylamino)benzoic acid] (2) reported by us previously. 34 Self-assembly under appropriate conditions led to formation a new hydrogen-bonded framework denoted as ZIOC-1.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Synthesis of 3,3′-Ethyne-1,2-diyl-bis[6-(L-prolylamino)benzoic acid] (EDPBA) (1). TMSCl (2.12 g, 19.56 mmol) was added to a solution of diarylacetylene 2 34 Self-Assembly of ZIOC-1. Self-assembly of ZIOC-1 material proceeded as follows.…”

Section: ■ Introductionmentioning

confidence: 99%

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New Chiral Hydrogen-Bonded Organic Framework Based on Substituted Diarylacetylene Dicarboxylic Acid

Veselovsky

Lozanova

Исаева

et al. 2020

Crystal Growth & Design

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A new chiral hydrogen-bonded organic framework (HOF) denoted as ZIOC-1 based on a l-prolineamide substituted diarylacetylene dicarboxylic acid (3,3′-ethyne-1,2-diylbis[6-(l-prolylamino)benzoic acid]) has been synthesized and structurally characterized. Crystal structures of two forms of ZIOC-1, i.e., anhydrous and dihydrate phases, were identified by powder X-ray analysis. It was found that the novel HOF material demonstrated a framework flexibility: its crystalline phases transform reversibly into each other by a change in either humidity or ambient temperature. This fact in conjunction with the retention of crystal identity to the temperature as high as 265 °C indicates a robustness of the framework formed by a hydrogen bonding system. The catalytic performance of the synthesized HOF was probed in aldol condensation and Michael reaction.

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