Synthesis of polyisoprene terpenoid dendrons and their applications in oligo(phenylene ethynylene)s as "shells".
The novel double-stage convergent synthesis of a new class of polyisoprene terpenoid (PIPTP) dendrons is described. PIPTP dendrons bear a highly branched aliphatic hydrocarbon skeleton and a hydrophilic hydroxy focal point functionality. These dendrons have the specific formula C((5×2)(G+1)(-5))H((5×2)(G+2)(-8))O, and each dendritic layer is constructed from an isoprene unit. The key branching steps involve a double alkyl-metal addition to an ester functionality, followed by deoxygenation of the resulting tertiary alcohol by triethylsilane and trifluoroacetic acid, then hydrogenation or hydrogenolysis. The dendrons were also attached to oligo(phenylene ethynylene)s (OPEs) so as to function as protective shells to allow fine tuning of the nanoscopic environment around the OPE moiety, and to exert precise control of the packing density and intermolecular interaction between the OPE cores. Fluorescence quantum yield data reveal that the OPE core is better encapsulated by the PIPTP dendrons than by Fréchet dendrons.
State Key Laboratory of Applied Organic Chemistry and College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, PR China.
Wen-Yu
WY
Chai
Zi-Fa
ZF
Shi
Peng
P
An
Wei
W
Wang
Lu-Feng
LF
Wang
Xiao-Ping
XP
Cao
D000480:Alkynes / Q000138:chemical synthesis* / Q000737:chemistry; D050091:Dendrimers / Q000138:chemical synthesis* / Q000737:chemistry; D004987:Ethers / Q000138:chemical synthesis* / Q000737:chemistry; D045782:Hemiterpenes / Q000138:chemical synthesis* / Q000737:chemistry; D007840:Latex / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013729:Terpenes / Q000138:chemical synthesis* / Q000737:chemistry
D000480:Alkynes; D050091:Dendrimers; D004987:Ethers; D045782:Hemiterpenes; D007840:Latex; D013729:Terpenes; C436384:phenyleneethynylene; C455100:1,4-polyisoprene