PMID- 35912912
OWN - NLM
STAT- MEDLINE
DCOM- 20221007
LR  - 20221011
IS  - 1861-471X (Electronic)
IS  - 1861-471X (Linking)
VI  - 17
IP  - 19
DP  - 2022 Oct 4
TI  - Supramolecular Gels from Bis-amides of L-Phenylalanine: Synthesis, Structure and 
      Material Applications.
PG  - e202200660
LID - 10.1002/asia.202200660 [doi]
AB  - A series of small organic molecules having a bis-amide backbone containing 
      hydrogen-bond functionalities were rationally designed, synthesized and 
      characterized to examine their ability to act as potential low-molecular-weight 
      gelators (LMWGs). All the bis-amides were decorated with identical 3-pyridyl 
      amide of L-phenylalanine moieties along with variously substituted terminal 
      benzoyl groups. Gelation studies revealed that only 4-methylphenyl substituted 
      bis-amide (PME) was capable of gelling both aqueous (DMSO/water) and methyl 
      salicylate (MS) (an important solvent for topical formulation for medical 
      applications) solvents; whereas 4-chlorophenyl and 4-bromophenyl substituted 
      bis-amides (PCL, PBR, respectively) acted as organogelator for various organic 
      solvents. On the contrary, 4-nitrophenyl as well as 3,5-dinitrophenyl substituted 
      bis-amides (PNI, DNI, respectively) were unable to gel any solvents studied 
      herein. The corresponding aqueous gel namely PME-HG and three methyl salicylate 
      gels PME-MS, PCL-MS and PBR-MS were characterized by dynamic and table top 
      rheology followed by electron microscopy. Single crystal X-ray diffraction (SXRD) 
      data revealed crucial insights into the supramolecular assembly of all the 
      gelator and nongelator bis-amides. Both PME-HG and PME-MS were rheoreversible - 
      an important property in material applications. Interestingly, PME-MS displayed 
      remarkable material properties such as shape-sustaining, loadbearing and 
      self-healing. Selected MS and aqueous gels loaded with nano-molar iodine were 
      found to possess anti-bacterial property as revealed by zone inhibition assay.
CI  - (c) 2022 Wiley-VCH GmbH.
FAU - Manna, Utsab
AU  - Manna U
AUID- ORCID: 0000-0001-9242-5812
AD  - School of Chemical Sciences, Indian Association for the Cultivation of Science, 
      2A & 2B Raja S. C. Mullick Road, Kolkata, 700032, India.
FAU - Roy, Rajdip
AU  - Roy R
AD  - School of Chemical Sciences, Indian Association for the Cultivation of Science, 
      2A & 2B Raja S. C. Mullick Road, Kolkata, 700032, India.
FAU - Datta, Hemanta Kumar
AU  - Datta HK
AUID- ORCID: 0000-0002-6466-6464
AD  - School of Chemical Sciences, Indian Association for the Cultivation of Science, 
      2A & 2B Raja S. C. Mullick Road, Kolkata, 700032, India.
FAU - Dastidar, Parthasarathi
AU  - Dastidar P
AUID- ORCID: 0000-0002-1011-2386
AD  - School of Chemical Sciences, Indian Association for the Cultivation of Science, 
      2A & 2B Raja S. C. Mullick Road, Kolkata, 700032, India.
LA  - eng
GR  - DST-SERB, India/
GR  - 02(0402)/21/EMR-II/CSIR, New Delhi/
GR  - IACS/
PT  - Journal Article
DEP - 20220818
PL  - Germany
TA  - Chem Asian J
JT  - Chemistry, an Asian journal
JID - 101294643
RN  - 0 (Amides)
RN  - 0 (Gels)
RN  - 0 (Salicylates)
RN  - 0 (Solvents)
RN  - 059QF0KO0R (Water)
RN  - 47E5O17Y3R (Phenylalanine)
RN  - 7YNJ3PO35Z (Hydrogen)
RN  - 9679TC07X4 (Iodine)
RN  - LAV5U5022Y (methyl salicylate)
RN  - YOW8V9698H (Dimethyl Sulfoxide)
SB  - IM
MH  - *Amides/chemistry
MH  - Dimethyl Sulfoxide
MH  - Gels/chemistry
MH  - Hydrogen
MH  - *Iodine
MH  - Phenylalanine/chemistry
MH  - Salicylates
MH  - Solvents/chemistry
MH  - Water
OTO - NOTNLM
OT  - Aqueous gel
OT  - LMWGs
OT  - Methyl salicylate gel
OT  - Rheoreversibility
OT  - Supramolecular gels
EDAT- 2022/08/02 06:00
MHDA- 2022/10/12 06:00
CRDT- 2022/08/01 06:24
PHST- 2022/07/25 00:00 [revised]
PHST- 2022/06/23 00:00 [received]
PHST- 2022/08/02 06:00 [pubmed]
PHST- 2022/10/12 06:00 [medline]
PHST- 2022/08/01 06:24 [entrez]
AID - 10.1002/asia.202200660 [doi]
PST - ppublish
SO  - Chem Asian J. 2022 Oct 4;17(19):e202200660. doi: 10.1002/asia.202200660. Epub 
      2022 Aug 18.