Enabling three-dimensional porous architectures via carbonyl functionalization and molecular-specific organic-SERS platforms

Ibrahim Deneme, Gorkem Liman, Ayse Can, Gokhan Demirel () and Hakan Usta ()
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Ibrahim Deneme: Abdullah Gül University
Gorkem Liman: Bio-inspired Materials Research Laboratory (BIMREL), Department of Chemistry, Gazi University
Ayse Can: Abdullah Gül University
Gokhan Demirel: Bio-inspired Materials Research Laboratory (BIMREL), Department of Chemistry, Gazi University
Hakan Usta: Abdullah Gül University

Nature Communications, 2021, vol. 12, issue 1, 1-11

Abstract: Abstract Molecular engineering via functionalization has been a great tool to tune noncovalent intermolecular interactions. Herein, we demonstrate three-dimensional highly crystalline nanostructured D(C7CO)-BTBT films via carbonyl-functionalization of a fused thienoacene π-system, and strong Raman signal enhancements in Surface-Enhanced Raman Spectroscopy (SERS) are realized. The small molecule could be prepared on the gram scale with a facile synthesis-purification. In the engineered films, polar functionalization induces favorable out-of-plane crystal growth via zigzag motif of dipolar C = O···C = O interactions and hydrogen bonds, and strengthens π-interactions. A unique two-stage film growth behavior is identified with an edge-on-to-face-on molecular orientation transition driven by hydrophobicity. The analysis of the electronic structures and the ratio of the anti-Stokes/Stokes SERS signals suggests that the π-extended/stabilized LUMOs with varied crystalline face-on orientations provide the key properties in the chemical enhancement mechanism. A molecule-specific Raman signal enhancement is also demonstrated on a high-LUMO organic platform. Our results demonstrate a promising guidance towards realizing low-cost SERS-active semiconducting materials, increasing structural versatility of organic-SERS platforms, and advancing molecule-specific sensing via molecular engineering.

Date: 2021
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DOI: 10.1038/s41467-021-26385-7

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