TTF derivative of 2,5-aromatic disubstituted pyrroles, experimental and theoretical study
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TTF derivative of 2,5-aromatic disubstituted pyrroles, experimental and theoretical study Lioudmila Fomina1, Christopher León1, Montserrat Bizarro1, Alejandro Baeza2, Victoria Gómez-Vidales3, Luis E. Sansores1 and Roberto Salcedo1 1
Instituto de Investigaciones en Materiales, Universidad Nacional Autónoma de México, Circuito Exterior s/n. C.U. A. Postal 70-360, Delegación Coyoacán. C.P. 04510. México D.F., México 2 Facultad de Química, Universidad Nacional Autónoma de México, Circuito, Escolar s/n, Ciudad Universitaria, Coyoacán 04510, México D.F., México 3 Instituto de Química, Universidad Nacional Autónoma de México, Circuito Exterior s/n, Ciudad Universitaria, Coyoacán 04510, México D.F., México ABSTRACT In the last decades the interest in organic conductors has growth, so they have become the object of study of many research groups that are interested in developing new materials with important conducting properties. The charge transfer complexes (CTC) represent an important kind of organic conductors, because they exhibit high conductivity values, as well as versatility for their design. In this work, the charge transfer complex (CTC) formed by substituted pyrrole and tetrathiofulvalene (TTF) was obtained by means electrochemical synthesis, the resultant colored mix was characterized by Mass spectrometry, NMR and EPR studies, its intrinsic electronic behavior was measured by a four point probe method, besides theoretical calculations were carried out on the possible structures of the resultant molecular adduct. All the results show that there is a net transfer of an electron between both organic moieties in a solution giving place to a semiconductor species. INTRODUCTION The study of electronic materials has been growing and opening new important areas [1-3], the study of this kind of compounds takes account mainly on the energy of the highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) levels and the orbital interactions. These last interactions are fundamental for the communication between two different pair of molecules that can show interesting electronic interchanges [4]. The combination of TTF (tetrathiafulvalene) (Fig. 1) with several organic molecules showing electron donor-acceptor and charge transfer complexing abilities has given place to several interesting chemical mixes with important semiconducting behavior [3-7].
Fig. 1. Molecular structures of TTF (a) and 1-(4-nitrophenyl)-2,5-diphenyl-pyrrole (b) studied in this work.
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TTF molecule is known since 1970 [8-10] and one of the groups interested in its synthesis was the one to find the very important redox behavior of this substance [10]. The authors [10] suggest for the first time that the molecule can reach an aromatic situation on the consecutive lack of two electrons (Fig. 2), ther
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