JOURNAL ARTICLE
RESEARCH SUPPORT, NON-U.S. GOV'T
RESEARCH SUPPORT, U.S. GOV'T, NON-P.H.S.
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Two-Dimensional versus Three-Dimensional Self-Assembly of a Series of 5-Alkoxyisophthalic Acids.

Physisorbed self-assembled monolayers (SAMs) have been suggested as potential models for three-dimensional (3D) crystallization. This work studies the effect of altering the chain length of 5-alkoxyisophthalic acid (C n ISA) on self-assembled morphology in both two-dimensional (2D) and 3D to explore the extent comparisons can be drawn between dimensions. Previous studies of 5-alkoxyisophthalic acid at solid-liquid interfaces (2D) reported different morphologies for C5 ISA and C6 ISA-alkoxy chains on the one hand and C10 ISA and C18 ISA on the other. Independently, also in 3D a dependence of morphology on chain length has been reported, including an unexpected inclusion of a solvent in the 3D morphology of C6 ISA, while the previous reports of 2D self-assembly were driven only by molecule-molecule and molecule-substrate interactions. However, a complete set of data for comparison has been missing. Here, we report scanning tunneling microscopy (STM) and molecular dynamics simulations performed for C2 ISA self-assembled monolayers (SAMs) and STM imaging of C6 ISA-C9 ISA SAMs, to further examine self-assembly behavior in 2D. In 3D, X-ray diffraction analysis of C2 ISA single crystals was carried out to complete the data set. With a complete set of data, it was observed that regardless of the dimension, short-chain-length C n ISAs formed H-bonding-dominated structures, mid-chain-length C n ISAs exhibited solvent-dependent morphologies, and long-chain-length C n ISAs displayed van der Waals-dominated solvent-independent structures. However, the transition point among morphologies occurred at different chain lengths in 2D and 3D regardless of the dominant interaction. The results of this study inform the design of 2D films and guide the application of knowledge from physisorbed SAMs to 3D systems, including mixed-dimensional (2D/3D) van der Waals heterostructures.

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