Porous Organic Material from Discotic Tricarboxyamide: Side Chain–Core interactions

Abstract

The benzene-1,3,5-tricarboxyamide containing three l-methionine (1) self-assemble through 3-fold amide-amide hydrogen bonds and π-π stacking to fabricate one-dimensional nanorod like structure. However, the tyrosine analogue (2) carrying multiple H-bonding side chains lost the C3 symmetry and 3-fold amide-amide hydrogen bonds and developed a porous structure. The porous material exhibits ten times more N2 sorption (155 cc/g) than the columnar one, indicating that side chain-core interactions have a drastic effect on structure and function.

Adaptive Correction from Virtually Complex Dynamic Libraries: The Role of Noncovalent Interactions in Structural Selection and Folding

“…Substitution of the central tripodalb uildingb lock by ar elated tricarboxylic acid with ad ifferent geometrical disposition was also performed. [32] The use of cyclohexanetricarboxylic derivative 1b had am ajor impact on the mixture containing just this moiety and ab ipodal structure. Thus,avery complex HPLC-tracew as obtained.…”

Coordination chemistry of flexible benzene-1,3,5-tricarboxamide derived carboxylates; notable structural resilience and vaguely familiar packing motifs

“…12,16 In particular, the dominant aggregation mode can be influenced away from the classic threefold hydrogen bonded helix in the presence of competing hydrogen bond donors or other directing forces, as we among others have recently demonstrated. [12][13][14]17 Controlling the aggregation mode of BTA derivatives has been particularly important in directing the formation of discotic liquid crystalline mesophases, 18 as well as functional supramolecular gels, with columnar aggregation prominent in both instances. [12][13][14]19 As with most polytopic scaffolds, BTA derivatives have recently seen increasing use as ligands in coordination polymers and discrete metallocages.…”

“…[12][13][14]19 As with most polytopic scaffolds, BTA derivatives have recently seen increasing use as ligands in coordination polymers and discrete metallocages. In the former, and keeping with conventional wisdom, rigid side chains are strongly represented, 20 along with amino acids, 17 while in the latter case, flexible chains terminated with N-donor ligands have been used to great success. 21 Underrepresented, however, are instances of extended structures from BTA derivatives with both large bridging distances between metal binding sites and inherent side-chain flexibility.…”

Porous Biomaterials via Side Chain‐Side Chain Interactions of Tyrosine Analogue of Pyridine Carboxamides

“…Inspired by this concept, we decided to study the significance of sidechain / sidechain correspondence in double helical architectural stabilization and thereafter its control over porous properties. However till date, only little effort have been devoted in peptide based porous biomaterial design using sidechains ,. Thus, knowing the ability of 2,6 pyridinedicarboxylic acid to nucleate double helical structures, our objective lied to probe the following aspects: a) replace the methyl side chain in Ala (Pseudopeptide I) by Tyr, bearing additional H‐bonding units (phenolic OH) in the dipeptidyl fragment (Pseudopeptide II) and explore the solid and solution conformations; b) Study the aggregation behavior of the pseudopeptide (Pseudopeptide III) originating due to replacement of Tyr‐ m ABA fragment by Ile‐Tyr (Figure ); c) Decipher the gas adsorption properties to determine whether sidechain/sidechain interactions play any role in governing porous properties.…”