Molecular solar thermal (MOST) energy storage systems based on the norbornadiene-quadricyclane pair show promise as next generation solar energy harvesting materials due to high energy storage capacity and reversibility of the photoisomerization reaction that enables repeating cycles and continuous conversion of sunlight to heat. Only a few recent reports explore the norbornadiene-quadricyclane system on a solid support (metals, HOPG), noting that the back-conversion reaction can be performed catalytically (by a metal surface) or electrocatalytically (by applying potential). Our cutting edge approach is to harvest, store and release energy using molecular monolayers on surfaces, and for that we will combine the norbornadiene-quadricyclane antenna with diamondoid anchor units. Diamondoids, cage hydrocarbons that can be selectively chemically functionalized, are used as molecular building blocks in nanomaterials design and can self-assemble on surfaces to form ordered 2D monolayers due to London dispersion interactions acting between them. We previously introduced a new approach to constructing larger diamondoid systems by preparing diamondoid covalent assemblies with a heteroatom linker. Here we will synthesize novel diamondoid norbornadiene compound classes, deposit them on surfaces (metals, HOPG, etc.), study their spontaneous on-surface self-assembly (experimentally and computationally) and evaluate their applicability as MOST energy storage candidates by performing appropriate analytical measurements. Diamondoid MOST molecules are envisioned to possess increased system on-surface assembly (ordered monolayer formation), durability (negligible material decomposition), controllability (modulation with applied potential) and selectivity (straightforward chemical interconversion between the photoisomers), paving a way towards applicable MOST reactor devices as organic solar batteries/work generators.