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新型5'-芳基取代的2,5-双(3-癸基-2,2'-联噻吩-5-基)-1,3,4-恶二唑的合成及光学性质

Synthesis and optical properties of new 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles.

作者信息

Kostyuchenko Anastasia Sergeevna, Zheleznova Tatyana Yu, Stasyuk Anton Jaroslavovich, Kurowska Aleksandra, Domagala Wojciech, Pron Adam, Fisyuk Alexander S

机构信息

Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, 644050 Omsk, Russian Federation; Department of Organic Chemistry, Faculty of Science, RUDN University, 6 Miklukho-Maklaya st., 117198 Moscow, Russian Federation.

Laboratory of New Organic Materials, Omsk State Technical University, Mira Ave, 11, 644050 Omsk, Russian Federation.

出版信息

Beilstein J Org Chem. 2017 Feb 17;13:313-322. doi: 10.3762/bjoc.13.34. eCollection 2017.

DOI:10.3762/bjoc.13.34
PMID:28326140
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5331275/
Abstract

New photoluminescent donor-acceptor-donor (DAD) molecules, namely 5'-aryl-substituted 2,5-bis(3-decyl-2,2'-bithiophen-5-yl)-1,3,4-oxadiazoles were prepared by palladium-catalyzed coupling from readily available compounds such as ethyl 3-decyl-2,2'-bithiophene-5-carboxylate and aryl halides. The obtained compounds feature increasing bathochromic shifts in their emission spectra with increasing aryl-substituent size yielding blue to bluish-green emissions. At the same time, their absorption spectra are almost independent from the identity of the terminal substituent with λ values ranging from 395 to 405 nm. The observed trends are perfectly predicted by quantum chemical DFT/TDDFT calculations carried out for these new molecules.

摘要

新型光致发光供体-受体-供体（DAD）分子，即5'-芳基取代的2,5-双（3-癸基-2,2'-联噻吩-5-基）-1,3,4-恶二唑，是通过钯催化偶联由易于获得的化合物（如3-癸基-2,2'-联噻吩-5-羧酸乙酯和芳基卤化物）制备而成。所得到的化合物在发射光谱中呈现出随着芳基取代基尺寸增加而出现的红移增加现象，产生蓝色至蓝绿色发射。同时，它们的吸收光谱几乎与末端取代基的性质无关，λ值范围为395至405nm。对这些新分子进行的量子化学DFT/TDDFT计算完美地预测了所观察到的趋势。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/401f555fcd48/Beilstein_J_Org_Chem-13-313-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/288b3cb29484/Beilstein_J_Org_Chem-13-313-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/b00be8e50600/Beilstein_J_Org_Chem-13-313-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/150bcf57e4e2/Beilstein_J_Org_Chem-13-313-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/f8973376d44b/Beilstein_J_Org_Chem-13-313-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/1a71a90aff5a/Beilstein_J_Org_Chem-13-313-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/c5d069091118/Beilstein_J_Org_Chem-13-313-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/ac6a090848b8/Beilstein_J_Org_Chem-13-313-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/401f555fcd48/Beilstein_J_Org_Chem-13-313-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/288b3cb29484/Beilstein_J_Org_Chem-13-313-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/b00be8e50600/Beilstein_J_Org_Chem-13-313-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/150bcf57e4e2/Beilstein_J_Org_Chem-13-313-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/f8973376d44b/Beilstein_J_Org_Chem-13-313-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/1a71a90aff5a/Beilstein_J_Org_Chem-13-313-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/c5d069091118/Beilstein_J_Org_Chem-13-313-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/ac6a090848b8/Beilstein_J_Org_Chem-13-313-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/7796/5331275/401f555fcd48/Beilstein_J_Org_Chem-13-313-g005.jpg

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