Synthesis, Structure, and Properties of 4,7‐Dimethoxybenzo[c]tellurophene: A Molecular Pyroelectric Material

Thermal and Photoreductive Elimination from the Tellurium Center of π-Conjugated Tellurophenes

“…Tellurophene, the tellurium analogue of thiophene, is of interest as an organic electronic material due to favorable optoelectronic properties such as a narrow optical gap, large dielectric constant, high polarizability, and the ability to form close intramolecular interactions. − The reactivity of the tellurium center and its potential utility as a catalyst, however, have not been extensively studied. Our group has reported the oxidative addition of bromine to a tellurium-containing polymer and 2,5-substituted tellurophene small molecule with extended π-conjugation .…”

Synthesis, Structure, and Electropolymerization of 3,4-Dimethoxytellurophene: Comparison with Selenium Analogue

“…The lack of research on polytellurophenes is most probably due to the unavailability of suitable synthetic methodologies for the preparation of substituted tellurophene-based monomeric precursors . Consequently, very few substituted tellurophenes with accessible 2,5-positions are known …”

Synthesis of Benzo[c] and Naphtho[c]heterocycle Diesters and Dinitriles via Homoelongation

“…After being stirred for 1 h at room temperature, the reaction was directly concentrated in vacuo and the residue was purified with flash chromatography (CH 2 Cl 2 /hexane=9/1) to give the pure diester product (62 mg, 31%): 1 H NMR (400 MHz, CDCl 3 ) δ (s, 2 H), 7.85 (s, 2 H), 4.35 (q, J=7.1 Hz, 4 H), 1.36 (t, J=7.1 Hz, 6 H); 13 C NMR (125 MHz, CDCl 3 ) δ 167. 81, 136.53, 126.81, 124.81, 120.64, 61.34, 14.12 Benzo [c]thiophene-5,6-dicarbonitrile (5). The dialdehyde 2 (100 mg, 0.71 mmol) and fumaronitrile (84 mg, 1.08 mmol) were dissolved in CH 2 Cl 2 (4 mL), and the solution was immersed in an ice bath.…”

“…The reaction was stirred at room temperature for 16 h. The reaction was then concentrated, and the remaining crude product was purified on flash chromatography (CH 2 Cl 2 /hexane=4/1) to give the diester 6 as a yellow solid (907 mg, 60%): IR (KBr) ν (cm -1 ) 3057, 2982,1721,1283,1243,1114,761,690; 1 H NMR (400 MHz, CDCl 3 ) δ 8.27 (s, 2 H), 7.93 (d, J=7.9 Hz, 4 H), 7.51 (dd, J=7.9, 7. 5 Hz, 4 H), 7.36 (t, J=7.5 Hz, 2 H), 4.37 (q, J=7.1 Hz, 4 H), 1.38 (t, J=7.1 Hz, 6 H); 13 C NMR (100 MHz, CDCl 3 ) δ 167. 88, 146.86, 130.66, 129.37, 128.70, 128.37, 125.58, 124.33, 120.44, 61.80, 14.42; FAB þ -HRMS (M þ ) calcd for C 26 H 22 O 5 414.1467, found 414.1464.…”

“…4 More recently, pyroelectric property has been found in some tellurophene derivatives. 5 Computational study also identified naphtho [c]heterocycles as good candidates for light-harvesting dyes in solar cell. 6 Yet, despite such a rich heritage, the synthetic routes to these benzo [c]heterocycles are quite limited.…”