Effect of substituents on mutual induced-fit controlled hydrogen-bonded capsule formation

Singh, Ashutosh Sharan, Kaur, Sarvjeet (2025). Effect of substituents on mutual induced-fit controlled hydrogen-bonded capsule formation. oai:ojs2.pubs.rsyn.org:article/128

Singh, Ashutosh Sharan, Kaur, Sarvjeet. "Effect of substituents on mutual induced-fit controlled hydrogen-bonded capsule formation.".

Singh, Ashutosh Sharan, Kaur, Sarvjeet. "Effect of substituents on mutual induced-fit controlled hydrogen-bonded capsule formation.".

@article{singh2025effect,
  title = {Effect of substituents on mutual induced-fit controlled hydrogen-bonded capsule formation},
  author = {Singh, Ashutosh Sharan and Kaur, Sarvjeet},
  year = 2025,
  journal = {},
  url = oai:ojs2.pubs.rsyn.org:article/128,
  language = en
}

TY  - JOUR
TI  - Effect of substituents on mutual induced-fit controlled hydrogen-bonded capsule formation
AU  - Singh, Ashutosh Sharan
AU  - Kaur, Sarvjeet
PY  - 2025
DA  - 2025-04-03
UR  - oai:ojs2.pubs.rsyn.org:article/128
AB  - The mutual induced-fit process, well known in biological systems, involves the cooperative interaction of multiple components. However, mimicking this process in artificial systems, particularly using purely organic components, presents a significant challenge. In this study, we explore the role of substituents in enhancing the mutual induced-fit effect, leading to signal amplification in hydrogen-bonded capsule formation. Two distinct, highly flexible ligands an N-bridged tripodal ligand and a triazine-bridged ligand were employed. The N-bridged ligand acts as a molecular clip, inducing a cone-shaped conformation in the triazine-bridged adduct. This conformation undergoes solvent polarity-dependent hydrogen-bonded capsule formation, yielding a single product. In the absence of the N-bridged ligand, only 50% capsule formation was observed through ¹H NMR at 100 mM concentration. However, in its presence, mutual interactions drive the system into a stable cone-shaped conformation, achieving 100% capsule formation, independent of concentration. The entire process is characterized by IR spectroscopy, ¹H and ¹³C NMR spectra, concentration-dependent ¹H NMR titration, ¹H-¹H COSY, ¹H-¹H NOESY, DOSY NMR, high-resolution ESI mass spectrometry, and energy-minimized structural analysis. 
LA  - en
ER  -