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. 2021 Aug 5;129:112356. doi: 10.1016/j.msec.2021.112356

Table 2.

The list of most suitable aromatic/surfactants/amphiphilic compounds for functionalization of graphene/rGo through noncovalent π–π interactions reported in the literature.

Surface functional molecule for non-covalent functionalization Carbon nanomaterial Interaction Reference
Pyridinium-functionalized porphyrin Graphene Size and planarity with graphene by π stacking [60]
Protoporphyrins of iron (FePP) and zinc (ZnPP) Graphene Large bandgap (0.45 eV) yielded bv FePP π–π stacking in graphene, while ZnPP physi-sorbed (0.23 eV). [61]
Porphyrin derivatives with sulfonate (negatively charged TPP-SO3Na) and ammonium groups (positively charges TPP-ammonium) rGO Non-covalent functionalization induced repulsive forces between the negative charges. [62]
3.4.9.10-perylenetetracarboxylic diimidebisbenzenesulfonicacid (PDI) -acceptor and Pyrene-1–sulfonic acid (Pys)-donor rGO Electron donor or acceptor π-π interactions for remarkable charge-transfer ability [65]
Different polar molecules: naphthalene, 1-napthylamine, and 1-naphthol GO/FeO.Fe2O3 and multi-walled carbon nanotubes (MWCNTs)/ FeO.Fe2O3 Polar nature of molecules with the adsorption ability [89]
Four pyrene units and a laterally-grafted oligo ether dendron Graphite exfoliation Tetrapyrene aromatic rings interacted with basal plane of graphene, hydrophilicity due to oligo ether chains [63]
Sulfonated pyrene derivatives:PS1(1-pyrenesulfonic acid sodium), PS2 (6,8-dihdroxy-1,3-pyrenedisulfonic acid disodium), PS3 (8-hydroxypyrene-1,3,6-trisulfonic acid trisodium) and PS4 (pyrene-1,3,6,8-tetrasulfonic acid tetrasodium) Graphite exfoliation PS2 is the most asymmetric functionalization with highest dipole moment for graphite exfoliation [64]
PS1: 1-pyrenesulfonic acid sodium salt In-situ exfoliation of graphite, graphene nanosheets (GNS) GNS surface decorated with functional molecules via with π–π stacking force [66]
1-pyrenecarboxylic acid (PCA) Graphite exfoliation into single-, few-, and multilayered graphene flakes PCA induces separation of graphitic layers with the help of its carboxylic groups and prevent π-stacking reform reversing. PCA also exhibits a hydrophobic pyrene group which mimics graphene with π-π interaction [67]
Lamination of PCA-functionalized graphene onto flexible-transparentpolydimethylsiloxane (PDMS) Multifunctional hybrid structure for electronic device [90]
Pyrene butanoic acid succidymidyl ester (PBSA) Few layers of CVD graphene Interactions (π − π) between PBSA and graphene [91]
Pyrenebutanoic acid-succinimidyl ester Noncovalent functionalization of Epitaxial graphene Graphene non-covalently binds with pyrene and succinimide ester reactive group [92]
1,3,6,8-pyrenetetrasulfonic acid (Py-SO3) tetrasodium hydrate,1-pyrenemethylamine (Py-NH2) hydrochloride Exfoliation of graphite Strong anchoring of planar aromatic structures of pyrene moles on hydrophobic graphene surface via π–π interactions yielding a stable graphene/pyrene hybrid [68]
Sulfonated aluminum phthalocyanine (aromatic planar component) GO, rGO, single wall carbon nanotubes (SWNTs) π–π interactions of aromatic planar component [93]
Pynidinium tribromide (aromatic with hydrophilic groups) highly oriented pyrolytic graphite (HOPG) Hydrophilic or lipophilic chains electrostatic repulsions [69]
Imidazolium ionic liquids (IL) with phyneyle:
  • •

    1-benzyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide (IL-1),

  • •

    1-butyl-3-methylimidazolium bis(trifluoromethylsulfonyl)amide (IL-2),

  • •

    1-benzyl-3-methylimidazolium bromide (IL-3), and

  • •

    1,3-bis(phenylmethyl)imidazolium bis(trifluoromethylsulfonyl)amide (IL-4)

 Graphene IL-4 exhibited most effective graphene stabilizer via π–π stacking with its two phenyl groups was [70]
1-allyl-methylimidazolium chloride ionic liquid rGO Prevented aggregation between graphene nanosheets with cation–π stacking/π–π interaction and electrostatic repulsion [71]
Hydrophilic ILs:
  • •

    1-alkyl-3-methyllimidazolium and N-alkylpyridinium

 rGO Dispersion and stabilization are the driving forces caused by the cation-π and/or π–π interactions [72]
Imidazolium salt (functional amphiphilic ionic liquid):
  • •

    1-(11-hydroxy-undecyl)-3-methyl-imidazolium-N-N-bis(trifluoromethane) sulphonamide (ImOH/TFSI)

 GO Interaction with imidazolium moieties and graphitic structure occur by π-cation stacking electrostatic interactions and post-reduction [73]
Two vinyl-benzyl groups containing imidazolium ionic liquids (Imi-ILs). GO Exchange of ions between -vely charged GO and + ve imidazolium of Imi-ILs. Imi-ILs attachment via non-covalent π-stacking on graphene [74]
Polymer IL-
  • •

    Poly(1-vinyl-3-ethylimidazolium)

 Exfoliation of graphite into graphene Interaction of GO sheet edges with -COO of imidazolium cations in PIL via electrostatic attractions and also cation−π and/or π − π interactions [75]
Quinoline Non oxidized graphene flakes (NOGFs) from exfoliation of graphite Binding of benzoic portion of quinoline to basal plane of NOGFs via strong via π–π interaction. [76]
9-anthracene carboxylic acid (ACA) Surface modification of rGO for enhanced electrochemical properties Stacking (π-π interaction) of the benzene ring in ACA anion on surface of rGO, while -COO− assisted their dispersion and water-solubility promoted by hydrogen bonding. [77]
Derivative of coronene (Anionic):
  • •

    Tetrapotassium salt of coronene tetracarboxylic acid (CS)

 Stabilization and functionalization of graphene sheet π-π stacking and non-covalent charge transfer between CS and graphene sheet [78]
Stabilizer C10:
  • •

    (2,3,6,7,10,11,-hexakis (10-caboxydecyloxy) triphenylene)

 Expanded graphite into few-layer graphene (FLG) dispersion C10, an amphiphilic aromatic molecule with core triphenylene six-acid groups. Strong affinity interaction between π-electron rich aromatic core and graphene via π–π interaction. [79]
Sodium dodecyl benzenesulfonate (SDBS) Exfoliation of graphite to graphene Anionic SDBS surfactant induce uniform dispersion in water preventing π-π stacking [81]
Ionic surfactants:
  • •

    Sodium dodecyl sulfate (SDS), SDBS

  • •

    4-(1,1,3,3-tetramethylbutyl)

Non-ionic:
  • •

    phenyl-polyethylene glycol (Triton X-100)

Diazoniums salts of sulfanilic acid:
  • •

    Quaternary ammonium salt (NPEQ)

  • •

    poly(ethylene glycol)

 Exfoliation, stable dispersion, surface modification GO, rGO SDBS modified rGO showed excellent dispersibility and electrical conductivity [80]
Exfoliation and surface modification of GO SO3− groups provided electrostatic repulsion, Sulfonated graphene forms a stable suspension followed by replacement of SO3− with a cationic nonylphenyl-PEG-quaternary ammonium salt (NPEQ) to form a stable suspension. [82]
Ionic surfactants:
  • •

    sodium deoxycholate (DOC)

  • •

    1-pyrenebutyric acid (PBA)

  • •

    sodium deoxycholate hydrate (TDOC)

  • •

    poly(sodium 4-styrenesulfonate) (PSS)

  • •

    SDBS

  • •

    SDS


Zwitterionic:
  • •

    3-((3-cholamidopropyl)dimethylammonium)1-propanesulfonate (CHAPS)

Non ionic:
  • •

    n-Dodecyl β-D-maltoside (DBDM)

  • •

    gum Arabic, pluronic®P-123

  • •

    Tween80

  • •

    Tween85 and

  • •

    polyvinylpyrrolidone (PVP)

 rGO stabilization Interaction of rGO with hydrophobic tail (alkyl vs. aromatic); or polar heads (sulfonic vs. carboxylic groups) of different surfactants. PSS and Tween 80 modified rGO exhibited significant increase in capacitance [85]
Sodium cholate Exfoliation of graphene Graphene interaction with carboxylic polar head groups [86]
Polyvinylpyrrolidone (non-ionic macromolecule) Exfoliation of graphite hydrophilic polymer confers exfoliation and colloidal stability graphene in water [84]
Anionic polysaccharide: Carboxymethyl cellulose (CMC) Porous rGO Active functional groups of CMC such as carbonyl and hydroxyl groups which show a strong affinity toward metal ions as well as stable dispersion [87]