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Title: Design, Synthesis, and Utility of Defined Molecular Scaffolds

Journal Article · · Organics
DOI: https://doi.org/10.3390/org2030013 · OSTI ID:1807607

A growing theme in chemistry is the joining of multiple organic molecular building blocks to create functional molecules. Diverse derivatizable structures—here termed “scaffolds” comprised of “hubs”—provide the foundation for systematic covalent organization of a rich variety of building blocks. This review encompasses 30 tri- or tetra-armed molecular hubs (e.g., triazine, lysine, arenes, dyes) that are used directly or in combination to give linear, cyclic, or branched scaffolds. Each scaffold is categorized by graph theory into one of 31 trees to express the molecular connectivity and overall architecture. Rational chemistry with exacting numbers of derivatizable sites is emphasized. The incorporation of water-solubilization motifs, robust or self-immolative linkers, enzymatically cleavable groups and functional appendages affords immense (and often late-stage) diversification of the scaffolds. Altogether, 107 target molecules are reviewed along with 19 syntheses to illustrate the distinctive chemistries for creating and derivatizing scaffolds. The review covers the history of the field up through 2020, briefly touching on statistically derivatized carriers employed in immunology as counterpoints to the rationally assembled and derivatized scaffolds here, although most citations are from the past two decades. The scaffolds are used widely in fields ranging from pure chemistry to artificial photosynthesis and biomedical sciences.

Sponsoring Organization:
USDOE
Grant/Contract Number:
FG02-05ER15661
OSTI ID:
1807607
Journal Information:
Organics, Journal Name: Organics Journal Issue: 3 Vol. 2; ISSN 2673-401X
Publisher:
MDPI AGCopyright Statement
Country of Publication:
Country unknown/Code not available
Language:
English

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The 8 year thicket of triazine dendrimers: strategies, targets and applications
  • Simanek, E. E.; Abdou, H.; Lalwani, S.
  • Proceedings of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 466, Issue 2117, p. 1445-1468 https://doi.org/10.1098/rspa.2009.0108
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