A kind of dithienocyclopentadiene derivative and preparation method thereof
A technology for dithienocyclopentadiene and derivatives is applied in the field of dithienocyclopentadiene derivatives and their preparation, and can solve the difficult preparation, harsh conditions and complicated routes of dithienocyclopentadiene derivatives and other problems, to achieve the effect of novel preparation, simple steps and wide application range
Active Publication Date: 2019-11-22
XIAN MODERN CHEM RES INST
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Problems solved by technology
[0006] In order to overcome the deficiencies and defects of the existing dithienocyclopentadiene derivatives, such as difficulties in preparation, cumbersome routes, and harsh conditions, the present invention provides a dithienocyclopentadiene derivative with fewer reaction steps, high reaction yield and multiple modification. Preparation method of cyclopentadiene derivative
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[0019] The present invention will be further explained by specific examples below.
[0020] The preparation route of dithienocyclopentadiene derivatives is shown below. Using 2-bromo-thiophene 1 and methyl 3-thiophenecarboxylate 2 as starting materials, intermediates 4a-4c are obtained through coupling and addition reactions in sequence , intermediates 4a-4c undergo a ring-closing reaction under the action of strong acid, and finally generate dithienocyclopentadiene derivatives 5a-5c. Intermediate 6 is obtained by controlling the amount of addition reaction metal reagent, and then through addition, closing The ring gives the unsymmetrical dithienocyclopentadiene derivative 8, see Examples for details.
[0021]
[0022] Preparation routes of dithienocyclopentadiene derivatives
[0023] Compound 3 synthetic route is as follows:
[0024]
[0025] Add 2-bromothiophene (1.96g, 12mmol), methyl 3-thiophenecarboxylate (1.42g, 10mmol), Pd(OAc) in a 50mL three-neck round bottom ...
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The invention belongs to the technical field of organic photoelectric materials and particularly relates to a dithienocyclopentadiene derivative and a preparation method thereof. The dithienocyclopentadiene derivative has the structural formula shown in the formula, wherein, R and R' represent C1-C20 alkyl groups, C1-C10 alkyl-substituted phenyl or C1-C10 alkyl-substituted thienyl. The preparationmethod comprises dissolving 2-bromothiophene, methyl 3-thiophene carboxylate and a base in an organic solvent, carrying out backflow for a reaction under action of a metal catalyst for 24h, carryingout a reaction process on the solution and an organometallic reagent, and carrying out ring closure with a strong acid to obtain a dithienocyclopentadiene derivative with a yield of 78-86%. The preparation method has the advantages of novel and simple processes, high yield and product separation and purification easiness. The dithienocyclopentadiene derivative contains multiple condensed rings, has strong conjugacy and can be used in the field of organic photoelectric materials.
Description
technical field [0001] The invention belongs to the field of organic photoelectric technology, and in particular relates to a dithienocyclopentadiene derivative and a preparation method thereof. Background technique [0002] After entering the 21st century, with the rapid development of the world economy, the energy problem has gradually become the main bottleneck of the sustainable development of various countries, and the effective use of renewable energy has become an urgent problem to be solved. Solar energy is an inexhaustible and inexhaustible source of energy. The current dominant photovoltaic technology is mainly based on inorganic materials, and its high material preparation cost and high energy consumption processing technology limit its wide application. Organic solar cells are photovoltaic devices mainly based on organic semiconductor carbon-based materials. Compared with inorganic solar cells, organic solar cells have low manufacturing cost, light material qual...
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IPC IPC(8): C07D495/04
Inventor 郭旺军周继华刘英哲刘亚东弥育华张杰宋新潮高潮
Owner XIAN MODERN CHEM RES INST