Journal: JACS Au

Article Title: Catalyst-Transfer Macrocyclization Protocol: Synthesis of π-Conjugated Azaparacyclophanes Made Easy

doi: 10.1021/jacsau.5c00109

Figure Lengend Snippet: Photographs series for the synthesis of APCs ( 1 ) performed under a controlled inert atmosphere (Example 1, inside a glovebox): a) reagents; b) weighing of precatalyst, ligand, and base in EPA vial; c) addition of THF; d) precatalyst mixture at the onset of activation; e) catalyst mixture after activation (1 h at 40 °C).

Article Snippet: Argon-filled glovebox with freezer (−39 °C) , MBraun , Labstar.

Techniques: Activation Assay

Journal: JACS Au

Article Title: Catalyst-Transfer Macrocyclization Protocol: Synthesis of π-Conjugated Azaparacyclophanes Made Easy

doi: 10.1021/jacsau.5c00109

Figure Lengend Snippet: Photographs series of APC ( 3 , Example 3) synthesis performed under standard laboratory settings, at the benchtop with the aid of a Schlenk line (outside the glovebox): a) weighing of precatalyst, ligand, and base in EPA vial; b) vessel evacuation/refilling with argon via Schlenk line; c) collection of anhydrous THF from an SPS; d) precatalyst mixture after addition of THF via syringe at the onset of activation; e) catalyst mixture after activation (1 h at 40 °C); f)–g) the sequence of addition of M3 into catalyst mixture via syringe; h) CTM reaction mixture after 2 h; i) quenching by injecting MeOH/HCl 1N (1:1 vol) into the reaction mixture to precipitate the product.

Article Snippet: Argon-filled glovebox with freezer (−39 °C) , MBraun , Labstar.

Techniques: Activation Assay, Sequencing

Journal: JACS Au

Article Title: Catalyst-Transfer Macrocyclization Protocol: Synthesis of π-Conjugated Azaparacyclophanes Made Easy

doi: 10.1021/jacsau.5c00109

Figure Lengend Snippet: Photographs series for the synthesis of APCs ( 1 ) performed under a controlled inert atmosphere (Example 1, inside a glovebox): a)–b) weighing of M1 in a weighing boat; c)–e) sequence of addition of M1 into catalyst mixture and closure of vial (note solution color change); CTM reaction mixture at f) onset of reaction, g) 1.5 h and h) 4 h (note the color and appearance changes).

Article Snippet: Argon-filled glovebox with freezer (−39 °C) , MBraun , Labstar.

Techniques: Sequencing

Journal: JACS Au

Article Title: Catalyst-Transfer Macrocyclization Protocol: Synthesis of π-Conjugated Azaparacyclophanes Made Easy

doi: 10.1021/jacsau.5c00109

Figure Lengend Snippet: Photographs series for the quenching and purification of APCs bulk materials ( 1 , Example 1) performed under standard laboratory settings in air (outside the glovebox): a)–c) sequence of quenching by injecting MeOH/HCl 1N (1:1 vol) into reaction mixture to precipitate the product (note the color and appearance changes); d) transfer of quenched mixture into a centrifuge tube; e) product plus washing solution after centrifugation (first cycle); f) sonication of product dispersed in a mixture of 2 mL distilled water and 12 mL MeOH (second cycle); g) product plus washing solution after centrifugation (second cycle); h) sonication of product dispersed in a mixture of 1 mL distilled water and 13 mL MeOH (third cycle); i) product plus washing solution after centrifugation (third cycle) for further decantation.

Article Snippet: Argon-filled glovebox with freezer (−39 °C) , MBraun , Labstar.

Techniques: Purification, Sequencing, Centrifugation, Sonication, Decantation Assay

Journal: JACS Au

Article Title: Catalyst-Transfer Macrocyclization Protocol: Synthesis of π-Conjugated Azaparacyclophanes Made Easy

doi: 10.1021/jacsau.5c00109

Figure Lengend Snippet: Equipment (Glovebox Experiments)

Article Snippet: Argon-filled glovebox with freezer (−39 °C) , MBraun , Labstar.

Techniques: Blocking Assay