Bio-based, self-organizing molecules are of considerable interest as optoelectronic materials due to their functionality that facilitates structural modifications, sophisticated structures that introduce chirality and their synthesis by mild-sustainable biocatalysis. This work is focused on molecules designed to mimic nature’s light-harvesting and self-aggregation characteristics for potential material applications as organic semiconductors and nonlinear optics. Among these potential candidates, photoactive porphyrin chromophores show promise for providing optoelectronic and highly tunable structure and morphology. In addition, a distinct class of microbially produced glycolipid biosurfactants known as sophorolipids show promise for providing the driving mechanism for self-assembly through carbohydrate hydrogen bonding groups, yielding supramolecular ribbon structures. Herein we explore a novel class of self-assembling functional compounds designed to exploit the self-organizing characteristics of sophorolipids with the natural light-harvesting abilities of porphyrin dyes. We report on spectroscopic studies of sophorolipid-porphyrin conjugated molecules in solution. Temperature-dependent linear absorption (UV-vis) spectra indicate the presence of self-aggregation while circular dichroism studies show the formation of helical J-aggregates. Comparative studies reveal that fine-tuning the distance between sophorolipid hydrogen-bonding sites and the porphyrin core alters the spectroscopic and self-assembled properties, providing insight into tunable pathways for optoelectronic and nonlinear optical materials.

Self-assembly of porphyrin conjugated sophorolipids for optoelectronic applications

254th National Meeting (2017)

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