Abstract
Furyl and thienyl moieties were introduced into a purine structure to elevate its fluorescence properties, while a trityl group was used to increase the amorphous properties of the purine compounds. The title compounds were prepared by a sequence involving a Mitsunobu, a SNAr and a Suzuki–Miyaura reaction and their photophysical properties were studied. Quantum yields in the solution reached up to 88% but only up to 5% in the thin layer.
Highlights
The synthesis and development of novel push–pull purine derivatives with potential as new materials and/or heavy metal sensors are currently in high demand [1]
A method for the synthesis of purine derivatives modified with furan and thiophene
A method for the synthesis of purine derivatives modified with furan and thiophene heterocycles heterocycles at C(8) has been developed
Summary
The synthesis and development of novel push–pull purine derivatives with potential as new materials and/or heavy metal sensors are currently in high demand [1]. In 2017, functionalized purine chromophores were developed using a Stille crosscoupling between 6-bromopurine and distannyl π-linkers of benzodithiophene, thiophene, or dithienylbenzothiadiazole [4]. These chromophores showed high thermal stability, long excited state lifetimes and high quantum yields, which will permit the use of such purine derivatives in material chemistry in the future. We have developed novel purine derivatives, containing a group at N(9) to enhance their amorphous properties [5], for study a fluorescent materials in thin films. 2-Iodothiophene was used for direct cross-coupling at the purine C(8) position in the presence of CuI and Pd(OAc) giving the 8-substitued product in 15% yield [8] The Sedlaček group successfully introduced a 2-thienyl group to the 9-substituted 2,6-diaminopurine using a Stille cross-coupling and a 3-thienyl group using a Suzuki–Miyaura reaction [7]. 2-Iodothiophene was used for direct cross-coupling at the purine C(8) position in the presence of CuI and Pd(OAc) giving the 8-substitued product in 15% yield [8]
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