Loading…
Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials
Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthal...
Saved in:
| Published in: | Tetrahedron 2016-08, Vol.72 (32), p.4918-4924 |
|---|---|
| Main Authors: | , , , , , , , , , , , , , |
| Format: | Article |
| Language: | English |
| Subjects: | |
| Citations: | Items that this one cites Items that cite this one |
| Online Access: | Get full text |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| cited_by | cdi_FETCH-LOGICAL-c373t-50b3052c11c42a2dc466a770c7fa24042a8b6b1f10db58ab98090302beda060f3 |
|---|---|
| cites | cdi_FETCH-LOGICAL-c373t-50b3052c11c42a2dc466a770c7fa24042a8b6b1f10db58ab98090302beda060f3 |
| container_end_page | 4924 |
| container_issue | 32 |
| container_start_page | 4918 |
| container_title | Tetrahedron |
| container_volume | 72 |
| creator | Yamamoto, Koji Takagi, Akuto Hada, Miyako Taniwaki, Ryosuke Mizutani, Tadashi Kimura, Yoshifumi Takao, Yuko Moriwaki, Kazuyuki Matsumoto, Fukashi Ito, Takatoshi Iwai, Toshiyuki Hida, Koichi Mizuno, Takumi Ohno, Toshinobu |
| description | Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthalocyanine by 0.13–0.39 eV. The optical band gap decreased in the order: hexafluoro->hexachloro->unsubstituted>hexaiodo-subnaphthalocyanine. Fluorescence quantum yield of hexaiodosubnaphthalocyanine was 0.05, significantly lower than those of the parent, hexafluoro- and hexachloro-subnaphthalocyanines whose quantum yields ranged from 0.2 to 0.22, indicating that the heavy atom effects of iodine work effectively.
[Display omitted] |
| doi_str_mv | 10.1016/j.tet.2016.06.064 |
| format | article |
| fullrecord | <record><control><sourceid>proquest_cross</sourceid><recordid>TN_cdi_proquest_miscellaneous_1835653157</recordid><sourceformat>XML</sourceformat><sourcesystem>PC</sourcesystem><els_id>S0040402016305968</els_id><sourcerecordid>1835653157</sourcerecordid><originalsourceid>FETCH-LOGICAL-c373t-50b3052c11c42a2dc466a770c7fa24042a8b6b1f10db58ab98090302beda060f3</originalsourceid><addsrcrecordid>eNp9UMtOwzAQtBBIlMIHcMuRS8L6kaQVJ1TxkpA4AGfLcTbEVWoH2wX69ziUAyeklWZ3NTPSDCHnFAoKtLpcFxFjwdJawDTigMyoqEReClodkhmAgFwAg2NyEsIaAChlfEY-n3c29hhMyJRtMzdGhwPq6J01Ohu9G9FHgyFzXdbjl9L94LzLf8jTbVzrwraxauxjrwand8oam_gqSfybmlz-GG5URG_UEE7JUZcAz35xTl5vb15W9_nj093D6vox17zmMS-h4VAyTakWTLFWi6pSdQ267hQTkH6LpmpoR6FtyoVqlgtYAgfWYKuggo7PycXeN0V532KIcmOCxmFQFt02SLrgZVVyWtaJSvdU7V0IHjs5erNRficpyKlkuZapZDmVLGEakTRXew2mDB8GvQzaoNXYGp9Cy9aZf9TfPVuIEA</addsrcrecordid><sourcetype>Aggregation Database</sourcetype><iscdi>true</iscdi><recordtype>article</recordtype><pqid>1835653157</pqid></control><display><type>article</type><title>Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials</title><source>ScienceDirect Journals</source><creator>Yamamoto, Koji ; Takagi, Akuto ; Hada, Miyako ; Taniwaki, Ryosuke ; Mizutani, Tadashi ; Kimura, Yoshifumi ; Takao, Yuko ; Moriwaki, Kazuyuki ; Matsumoto, Fukashi ; Ito, Takatoshi ; Iwai, Toshiyuki ; Hida, Koichi ; Mizuno, Takumi ; Ohno, Toshinobu</creator><creatorcontrib>Yamamoto, Koji ; Takagi, Akuto ; Hada, Miyako ; Taniwaki, Ryosuke ; Mizutani, Tadashi ; Kimura, Yoshifumi ; Takao, Yuko ; Moriwaki, Kazuyuki ; Matsumoto, Fukashi ; Ito, Takatoshi ; Iwai, Toshiyuki ; Hida, Koichi ; Mizuno, Takumi ; Ohno, Toshinobu</creatorcontrib><description>Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthalocyanine by 0.13–0.39 eV. The optical band gap decreased in the order: hexafluoro->hexachloro->unsubstituted>hexaiodo-subnaphthalocyanine. Fluorescence quantum yield of hexaiodosubnaphthalocyanine was 0.05, significantly lower than those of the parent, hexafluoro- and hexachloro-subnaphthalocyanines whose quantum yields ranged from 0.2 to 0.22, indicating that the heavy atom effects of iodine work effectively.
[Display omitted]</description><identifier>ISSN: 0040-4020</identifier><identifier>EISSN: 1464-5416</identifier><identifier>DOI: 10.1016/j.tet.2016.06.064</identifier><language>eng</language><publisher>Elsevier Ltd</publisher><subject>Absorption spectroscopy ; Dipole moment ; Electronics ; Fluorescence ; Halogen ; HOMO ; LUMO ; Molecular orbitals ; Optical property ; Optoelectronics ; Parents ; Solubility ; Subnaphthalocyanine ; Tetrahedrons</subject><ispartof>Tetrahedron, 2016-08, Vol.72 (32), p.4918-4924</ispartof><rights>2016 Elsevier Ltd</rights><lds50>peer_reviewed</lds50><oa>free_for_read</oa><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-c373t-50b3052c11c42a2dc466a770c7fa24042a8b6b1f10db58ab98090302beda060f3</citedby><cites>FETCH-LOGICAL-c373t-50b3052c11c42a2dc466a770c7fa24042a8b6b1f10db58ab98090302beda060f3</cites></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><link.rule.ids>314,780,784,27924,27925</link.rule.ids></links><search><creatorcontrib>Yamamoto, Koji</creatorcontrib><creatorcontrib>Takagi, Akuto</creatorcontrib><creatorcontrib>Hada, Miyako</creatorcontrib><creatorcontrib>Taniwaki, Ryosuke</creatorcontrib><creatorcontrib>Mizutani, Tadashi</creatorcontrib><creatorcontrib>Kimura, Yoshifumi</creatorcontrib><creatorcontrib>Takao, Yuko</creatorcontrib><creatorcontrib>Moriwaki, Kazuyuki</creatorcontrib><creatorcontrib>Matsumoto, Fukashi</creatorcontrib><creatorcontrib>Ito, Takatoshi</creatorcontrib><creatorcontrib>Iwai, Toshiyuki</creatorcontrib><creatorcontrib>Hida, Koichi</creatorcontrib><creatorcontrib>Mizuno, Takumi</creatorcontrib><creatorcontrib>Ohno, Toshinobu</creatorcontrib><title>Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials</title><title>Tetrahedron</title><description>Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthalocyanine by 0.13–0.39 eV. The optical band gap decreased in the order: hexafluoro->hexachloro->unsubstituted>hexaiodo-subnaphthalocyanine. Fluorescence quantum yield of hexaiodosubnaphthalocyanine was 0.05, significantly lower than those of the parent, hexafluoro- and hexachloro-subnaphthalocyanines whose quantum yields ranged from 0.2 to 0.22, indicating that the heavy atom effects of iodine work effectively.
[Display omitted]</description><subject>Absorption spectroscopy</subject><subject>Dipole moment</subject><subject>Electronics</subject><subject>Fluorescence</subject><subject>Halogen</subject><subject>HOMO</subject><subject>LUMO</subject><subject>Molecular orbitals</subject><subject>Optical property</subject><subject>Optoelectronics</subject><subject>Parents</subject><subject>Solubility</subject><subject>Subnaphthalocyanine</subject><subject>Tetrahedrons</subject><issn>0040-4020</issn><issn>1464-5416</issn><fulltext>true</fulltext><rsrctype>article</rsrctype><creationdate>2016</creationdate><recordtype>article</recordtype><recordid>eNp9UMtOwzAQtBBIlMIHcMuRS8L6kaQVJ1TxkpA4AGfLcTbEVWoH2wX69ziUAyeklWZ3NTPSDCHnFAoKtLpcFxFjwdJawDTigMyoqEReClodkhmAgFwAg2NyEsIaAChlfEY-n3c29hhMyJRtMzdGhwPq6J01Ohu9G9FHgyFzXdbjl9L94LzLf8jTbVzrwraxauxjrwand8oam_gqSfybmlz-GG5URG_UEE7JUZcAz35xTl5vb15W9_nj093D6vox17zmMS-h4VAyTakWTLFWi6pSdQ267hQTkH6LpmpoR6FtyoVqlgtYAgfWYKuggo7PycXeN0V532KIcmOCxmFQFt02SLrgZVVyWtaJSvdU7V0IHjs5erNRficpyKlkuZapZDmVLGEakTRXew2mDB8GvQzaoNXYGp9Cy9aZf9TfPVuIEA</recordid><startdate>20160811</startdate><enddate>20160811</enddate><creator>Yamamoto, Koji</creator><creator>Takagi, Akuto</creator><creator>Hada, Miyako</creator><creator>Taniwaki, Ryosuke</creator><creator>Mizutani, Tadashi</creator><creator>Kimura, Yoshifumi</creator><creator>Takao, Yuko</creator><creator>Moriwaki, Kazuyuki</creator><creator>Matsumoto, Fukashi</creator><creator>Ito, Takatoshi</creator><creator>Iwai, Toshiyuki</creator><creator>Hida, Koichi</creator><creator>Mizuno, Takumi</creator><creator>Ohno, Toshinobu</creator><general>Elsevier Ltd</general><scope>AAYXX</scope><scope>CITATION</scope><scope>7SR</scope><scope>7U5</scope><scope>8BQ</scope><scope>8FD</scope><scope>JG9</scope><scope>L7M</scope></search><sort><creationdate>20160811</creationdate><title>Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials</title><author>Yamamoto, Koji ; Takagi, Akuto ; Hada, Miyako ; Taniwaki, Ryosuke ; Mizutani, Tadashi ; Kimura, Yoshifumi ; Takao, Yuko ; Moriwaki, Kazuyuki ; Matsumoto, Fukashi ; Ito, Takatoshi ; Iwai, Toshiyuki ; Hida, Koichi ; Mizuno, Takumi ; Ohno, Toshinobu</author></sort><facets><frbrtype>5</frbrtype><frbrgroupid>cdi_FETCH-LOGICAL-c373t-50b3052c11c42a2dc466a770c7fa24042a8b6b1f10db58ab98090302beda060f3</frbrgroupid><rsrctype>articles</rsrctype><prefilter>articles</prefilter><language>eng</language><creationdate>2016</creationdate><topic>Absorption spectroscopy</topic><topic>Dipole moment</topic><topic>Electronics</topic><topic>Fluorescence</topic><topic>Halogen</topic><topic>HOMO</topic><topic>LUMO</topic><topic>Molecular orbitals</topic><topic>Optical property</topic><topic>Optoelectronics</topic><topic>Parents</topic><topic>Solubility</topic><topic>Subnaphthalocyanine</topic><topic>Tetrahedrons</topic><toplevel>peer_reviewed</toplevel><toplevel>online_resources</toplevel><creatorcontrib>Yamamoto, Koji</creatorcontrib><creatorcontrib>Takagi, Akuto</creatorcontrib><creatorcontrib>Hada, Miyako</creatorcontrib><creatorcontrib>Taniwaki, Ryosuke</creatorcontrib><creatorcontrib>Mizutani, Tadashi</creatorcontrib><creatorcontrib>Kimura, Yoshifumi</creatorcontrib><creatorcontrib>Takao, Yuko</creatorcontrib><creatorcontrib>Moriwaki, Kazuyuki</creatorcontrib><creatorcontrib>Matsumoto, Fukashi</creatorcontrib><creatorcontrib>Ito, Takatoshi</creatorcontrib><creatorcontrib>Iwai, Toshiyuki</creatorcontrib><creatorcontrib>Hida, Koichi</creatorcontrib><creatorcontrib>Mizuno, Takumi</creatorcontrib><creatorcontrib>Ohno, Toshinobu</creatorcontrib><collection>CrossRef</collection><collection>Engineered Materials Abstracts</collection><collection>Solid State and Superconductivity Abstracts</collection><collection>METADEX</collection><collection>Technology Research Database</collection><collection>Materials Research Database</collection><collection>Advanced Technologies Database with Aerospace</collection><jtitle>Tetrahedron</jtitle></facets><delivery><delcategory>Remote Search Resource</delcategory><fulltext>fulltext</fulltext></delivery><addata><au>Yamamoto, Koji</au><au>Takagi, Akuto</au><au>Hada, Miyako</au><au>Taniwaki, Ryosuke</au><au>Mizutani, Tadashi</au><au>Kimura, Yoshifumi</au><au>Takao, Yuko</au><au>Moriwaki, Kazuyuki</au><au>Matsumoto, Fukashi</au><au>Ito, Takatoshi</au><au>Iwai, Toshiyuki</au><au>Hida, Koichi</au><au>Mizuno, Takumi</au><au>Ohno, Toshinobu</au><format>journal</format><genre>article</genre><ristype>JOUR</ristype><atitle>Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials</atitle><jtitle>Tetrahedron</jtitle><date>2016-08-11</date><risdate>2016</risdate><volume>72</volume><issue>32</issue><spage>4918</spage><epage>4924</epage><pages>4918-4924</pages><issn>0040-4020</issn><eissn>1464-5416</eissn><abstract>Chloroboron(III) hexachloro- and hexaiodosubnaphthalocyanines were prepared, and their solubility, electronic absorption spectroscopy, fluorescence emission spectroscopy and HOMO/LUMO energy levels were evaluated. These subnaphthalocyanines showed lower HOMO/LUMO energies than the parent subnaphthalocyanine by 0.13–0.39 eV. The optical band gap decreased in the order: hexafluoro->hexachloro->unsubstituted>hexaiodo-subnaphthalocyanine. Fluorescence quantum yield of hexaiodosubnaphthalocyanine was 0.05, significantly lower than those of the parent, hexafluoro- and hexachloro-subnaphthalocyanines whose quantum yields ranged from 0.2 to 0.22, indicating that the heavy atom effects of iodine work effectively.
[Display omitted]</abstract><pub>Elsevier Ltd</pub><doi>10.1016/j.tet.2016.06.064</doi><tpages>7</tpages><oa>free_for_read</oa></addata></record> |
| fulltext | fulltext |
| identifier | ISSN: 0040-4020 |
| ispartof | Tetrahedron, 2016-08, Vol.72 (32), p.4918-4924 |
| issn | 0040-4020 1464-5416 |
| language | eng |
| recordid | cdi_proquest_miscellaneous_1835653157 |
| source | ScienceDirect Journals |
| subjects | Absorption spectroscopy Dipole moment Electronics Fluorescence Halogen HOMO LUMO Molecular orbitals Optical property Optoelectronics Parents Solubility Subnaphthalocyanine Tetrahedrons |
| title | Synthesis and optoelectronic properties of hexachloro- and hexaiodosubnaphthalocyanines as organic electronic materials |
| url | http://sfxeu10.hosted.exlibrisgroup.com/loughborough?ctx_ver=Z39.88-2004&ctx_enc=info:ofi/enc:UTF-8&ctx_tim=2025-01-05T22%3A16%3A47IST&url_ver=Z39.88-2004&url_ctx_fmt=infofi/fmt:kev:mtx:ctx&rfr_id=info:sid/primo.exlibrisgroup.com:primo3-Article-proquest_cross&rft_val_fmt=info:ofi/fmt:kev:mtx:journal&rft.genre=article&rft.atitle=Synthesis%20and%20optoelectronic%20properties%20of%20hexachloro-%20and%20hexaiodosubnaphthalocyanines%20as%20organic%20electronic%20materials&rft.jtitle=Tetrahedron&rft.au=Yamamoto,%20Koji&rft.date=2016-08-11&rft.volume=72&rft.issue=32&rft.spage=4918&rft.epage=4924&rft.pages=4918-4924&rft.issn=0040-4020&rft.eissn=1464-5416&rft_id=info:doi/10.1016/j.tet.2016.06.064&rft_dat=%3Cproquest_cross%3E1835653157%3C/proquest_cross%3E%3Cgrp_id%3Ecdi_FETCH-LOGICAL-c373t-50b3052c11c42a2dc466a770c7fa24042a8b6b1f10db58ab98090302beda060f3%3C/grp_id%3E%3Coa%3E%3C/oa%3E%3Curl%3E%3C/url%3E&rft_id=info:oai/&rft_pqid=1835653157&rft_id=info:pmid/&rfr_iscdi=true |