3,6-bis(hydroxymethyl)piperazine-2,5-dione

• CAS: 5625-41-2
• Catalog Number: ACM5625412
• Category: Main Products
• Molecular Weight: 174.2
• Molecular Formula: C6H10N2O4
• Melting Point: >208 ºC
• Appearance: White to Pale Yellow solid

Case Study

Application of 3,6-Bis(hydroxymethyl)piperazine-2,5-dione in the Synthesis of Reversibly Thermochromic Nanotubes

Seo, Min Jeong, et al. Langmuir 34.28 (2018): 8365-8373.

Cyclic dipeptides (CDPs) are attractive supramolecular headgroups because their backbone amides form strong intermolecular hydrogen-bond networks and chirality can direct helical packing. This study presented how 3,6-bis(hydroxymethyl)piperazine-2,5-dione (a dihydroxymethyl-substituted cyclic dipeptide core, available as cis and trans stereoisomers) serves as a headgroup for diacetylene-bearing amphiphiles that self-assemble into nanotubular architectures and, after UV-initiated topochemical polymerization, produce polydiacetylene (PDA) nanotubes that show reversible thermochromism (blue↔red) over multiple thermal cycles.
Synthetic Route: The CDP-diacetylene monomers were prepared by first converting PCDA to its acid chloride (oxalyl chloride/DMF, 0 °C → rt), then coupling the acid chloride to the dihydroxymethyl-piperazine-2,5-dione core in dichloromethane with pyridine as base at room temperature; workup involved acid triturations, aqueous washing, drying, and methanol washing to afford CDP-DA-2 (cis) in 23% yield and CDP-DA-3 (trans) in 22% yield under the conditions described.
Self-assembly and Morphology: When CDP-DA amphiphiles were assembled from a polar chloroform/methanol solvent system they organized into lamellar bilayers that underwent lamellar scrolling to produce both single- and multi-walled nanotubes.
Reversible Thermochromism: Exposure of the monomeric tubular assemblies to UV light producing blue-colored CDP/PDA nanotubes that exhibited a reversible blue-to-red color transition upon thermal cycling; this reversible thermochromism was reproducible for at least ten consecutive heating/cooling cycles.

Custom Q&A

What is the molecular formula of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The molecular formula is C6H10N2O4.

What is the molecular weight of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The molecular weight is 174.15 g/mol.

What are the synonyms of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The synonyms are 5625-41-2, 3,6-Bis(hydroxymethyl)-2,5-piperazinedione, Serinanhydrid, and L-serine dimer.

What is the IUPAC name of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The IUPAC name is 3,6-bis(hydroxymethyl)piperazine-2,5-dione.

What is the InChI of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The InChI is InChI=1S/C6H10N2O4/c9-1-3-5(11)8-4(2-10)6(12)7-3/h3-4,9-10H,1-2H2,(H,7,12)(H,8,11).

What is the InChIKey of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The InChIKey is SUWGHSHLNOADHI-UHFFFAOYSA-N.

What is the Canonical SMILES of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The Canonical SMILES is C(C1C(=O)NC(C(=O)N1)CO)O.

What is the CAS number of 3,6-bis(hydroxymethyl)piperazine-2,5-dione?

The CAS number is 5625-41-2.

How many hydrogen bond donor counts does 3,6-bis(hydroxymethyl)piperazine-2,5-dione have?

It has 4 hydrogen bond donor counts.

How many rotatable bond counts does 3,6-bis(hydroxymethyl)piperazine-2,5-dione have?

It has 2 rotatable bond counts.