[1] James Tour's research group designed and synthesized these compounds in 2003 as a part of a sequence on chemical education for young students.
Placing thiol (R-SH) functional groups at the end of the legs enables them to "stand" on a gold surface.
"NanoPutian" is a portmanteau of nanometer, a unit of length commonly used to measure chemical compounds, and lilliputian, a fictional race of humans in the novel Gulliver's Travels by Jonathan Swift.
Tour also received $100,000 in 2002 from the Small Grants for Exploratory Research program, a division of the National Science Foundation.
A 2004–2005 study in two schools districts in Ohio and Kentucky found that using NanoKids led to a 10–59% increase in understanding of the material presented.
Formylation of this structure was then achieved through using the organolithium reagent n-butyllithium followed by quenching with N,N-dimethylformamide (DMF) to create the aldehyde.
Originally, Chanteau and Tour aimed to couple this structure with alkynes, but this resulted in very low yields of the desired products.
To complete the synthesis of the lower body, the TMS protecting group is removed by selective deprotection through the addition of K2CO3, MeOH, and CH2Cl2 to yield 3,5-(1′-Pentynyl)-1-ethynylbenzene.
Most can be synthesized from the NanoKid by an acetal exchange reaction with the desired 1,2- or 1,3- diol, using p-toluenesulfonic acid as catalyst and heated by microwave irradiation for a few minutes.
The ultimate set of products was a recognizably diverse population of NanoPutians: NanoAthlete, NanoPilgrim, NanoGreenBeret, NanoJester, NanoMonarch, NanoTexan, NanoScholar, NanoBaker, and NanoChef.
[1] To make the NanoKid “stand’, the acetyl protecting groups were removed through the use of ammonium hydroxide in THF to create the free thiols.
One of the bromine substituents is converted to an aldehyde through an SN2 reaction with the strong base, n-BuLi, and THF in the aprotic polar solvent, DMF to produce 2,5-bis(4-tert-butyldimethylsiloxy-1′-butynyl)-4-bromobenzaldehyde.