Ionic Liquids (ILs) belong to a fascinating class of materials intensively studied and developed both for their fundamental interests and a hand full of technological applications due to their unique combination of tuneable-by-design properties such as low vapour pressure and flammability, high thermal and (electro)chemical stabilities, and ionic conductivity, to name a few. Encoding a liquid crystalline behaviour into the chemical structures of ILs allows for the dawn of stimuli-responsive (dynamically self-assembling/healing) functional materials, i.e. Thermotropic Ionic liquid Crystals (TILCs) . Interestingly, the ‘material marriage’ of ILs with thermotropic liquid crystals (TLCs) opens an exploratory research arena both for (i) in depth (fundamental) studies of the interplay linking the hierarchical self-assembly of functional soft matter into precise morphologies and (1D/2D/3D) dimensionality-controlled ionic transport properties and (ii) their technological uses as a key-enabling sub-component (i.e. the electrolyte) at the heart of new generations of safer-by-design (electrochemical) energy storage and conversion devices such as batteries & supercapacitors, and fuel cells, respectively. In this communication, we will detail the molecular design strategy, syntheses, and multi-scale structure/ionic transport correlations of a series of anionic conductors (A-TILCs) based on a di-n-octadecylimidazolium (C18C18Im+) cation with 4 anions, namely iodide [I-], bromide [Br-], bis(trifluoromethane)sulfonimide [TFSI-], and dicyanamide [N(CN)2-]. Relying on cross-fertilizing DSC, POM, and SAXS/WAXS characterizations, we will show that this series of A-TILCs share a lamellar organization (smectic A (SmA) mesophase) with ionophobic and ionophilic slabs encoding tuneable-by-design and nanoconfined 2D ionic transport. As reflected in their tuneable transition temperatures and ionic conductivity values (EIS), we will discuss how anion metathesis is authorizing the fine-tuning of A-TILCs. Finally, we will elaborate on the role of selected stimuli (e.g. electric/magnetic fields, light, etc.) to master mosaicity vs. long range order in TILCs (through on-demand control of their dynamic self-assembly) and the (growing) interest for self-healing into next generation energy storage/conversion devices. Acknowledgments: We are indebted to the French National Agency of Research (ANR) for the funding of the collaborative research project CITADEL under the grant ANR-19-CE05-0028. HP, MM & PR express their gratitude to CNRS & UGA for the support of the related research activities within the (Joint Research Unit) UMR5819-SyMMES & UMR5279-LEPMI labs.