Facile Syntheses, Characterization, and Physical Properties of Sulfur-Decorated Pyran-Annulated Perylene Diimides

Ran Wang; Gang Li; Yecheng Zhou; Pin Hao; Qiaoyan Shang; Shuaihua Wang; Yu Zhang; Dandan Li; Shufan Yang; Qichun Zhang; Zhiqiang Shi; Bo Tang

doi:10.1002/ajoc.201800011

Facile Syntheses, Characterization, and Physical Properties of Sulfur-Decorated Pyran-Annulated Perylene Diimides

Ran Wang, Gang Li^*, Yecheng Zhou, Pin Hao, Qiaoyan Shang, Shuaihua Wang, Yu Zhang, Dandan Li, Shufan Yang, Qichun Zhang^*, Zhiqiang Shi^*, Bo Tang^*

^*Corresponding author for this work

Research output: Journal Publications and Reviews › RGC 21 - Publication in refereed journal › peer-review

13 Citations (Scopus)

Abstract

Three sulfur-containing pyran-annulated perylene diimides (PDIs) were synthesized from commercially available PDIs through a nucleophilic substitution/cyclization reaction sequence. The as-synthesized compounds were fully characterized by ¹H and ¹³C NMR, and FT-IR spectroscopy, as well as HRMS and TGA. The as-prepared PDI derivatives exhibited significantly narrow HOMO–LUMO band gaps and high photochemical and thermal stability. Moreover, these materials exhibited quite different absorptions and emissions in dichloromethane, which were in agreement with the DFT-calculated results.

Original language	English
Pages (from-to)	702-706
Journal	Asian Journal of Organic Chemistry
Volume	7
Issue number	4
Online published	31 Jan 2018
DOIs	https://doi.org/10.1002/ajoc.201800011
Publication status	Published - Apr 2018
Externally published	Yes

Research Keywords

annulation
hydrocarbons
perylene diimides
polycycles
sulfur

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title = "Facile Syntheses, Characterization, and Physical Properties of Sulfur-Decorated Pyran-Annulated Perylene Diimides",

abstract = "Three sulfur-containing pyran-annulated perylene diimides (PDIs) were synthesized from commercially available PDIs through a nucleophilic substitution/cyclization reaction sequence. The as-synthesized compounds were fully characterized by 1H and 13C NMR, and FT-IR spectroscopy, as well as HRMS and TGA. The as-prepared PDI derivatives exhibited significantly narrow HOMO–LUMO band gaps and high photochemical and thermal stability. Moreover, these materials exhibited quite different absorptions and emissions in dichloromethane, which were in agreement with the DFT-calculated results.",

keywords = "annulation, hydrocarbons, perylene diimides, polycycles, sulfur, annulation, hydrocarbons, perylene diimides, polycycles, sulfur, annulation, hydrocarbons, perylene diimides, polycycles, sulfur",

author = "Ran Wang and Gang Li and Yecheng Zhou and Pin Hao and Qiaoyan Shang and Shuaihua Wang and Yu Zhang and Dandan Li and Shufan Yang and Qichun Zhang and Zhiqiang Shi and Bo Tang",

year = "2018",

month = apr,

doi = "10.1002/ajoc.201800011",

language = "English",

volume = "7",

pages = "702--706",

journal = "Asian Journal of Organic Chemistry",

issn = "2193-5807",

publisher = "John Wiley & Sons",

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TY - JOUR

T1 - Facile Syntheses, Characterization, and Physical Properties of Sulfur-Decorated Pyran-Annulated Perylene Diimides

AU - Wang, Ran

AU - Li, Gang

AU - Zhou, Yecheng

AU - Hao, Pin

AU - Shang, Qiaoyan

AU - Wang, Shuaihua

AU - Zhang, Yu

AU - Li, Dandan

AU - Yang, Shufan

AU - Zhang, Qichun

AU - Shi, Zhiqiang

AU - Tang, Bo

PY - 2018/4

Y1 - 2018/4

N2 - Three sulfur-containing pyran-annulated perylene diimides (PDIs) were synthesized from commercially available PDIs through a nucleophilic substitution/cyclization reaction sequence. The as-synthesized compounds were fully characterized by 1H and 13C NMR, and FT-IR spectroscopy, as well as HRMS and TGA. The as-prepared PDI derivatives exhibited significantly narrow HOMO–LUMO band gaps and high photochemical and thermal stability. Moreover, these materials exhibited quite different absorptions and emissions in dichloromethane, which were in agreement with the DFT-calculated results.

AB - Three sulfur-containing pyran-annulated perylene diimides (PDIs) were synthesized from commercially available PDIs through a nucleophilic substitution/cyclization reaction sequence. The as-synthesized compounds were fully characterized by 1H and 13C NMR, and FT-IR spectroscopy, as well as HRMS and TGA. The as-prepared PDI derivatives exhibited significantly narrow HOMO–LUMO band gaps and high photochemical and thermal stability. Moreover, these materials exhibited quite different absorptions and emissions in dichloromethane, which were in agreement with the DFT-calculated results.

KW - annulation

KW - hydrocarbons

KW - perylene diimides

KW - polycycles

KW - sulfur

KW - annulation

KW - hydrocarbons

KW - perylene diimides

KW - polycycles

KW - sulfur

KW - annulation

KW - hydrocarbons

KW - perylene diimides

KW - polycycles

KW - sulfur

UR - http://www.scopus.com/inward/record.url?scp=85045523412&partnerID=8YFLogxK

UR - https://www.scopus.com/record/pubmetrics.uri?eid=2-s2.0-85045523412&origin=recordpage

U2 - 10.1002/ajoc.201800011

DO - 10.1002/ajoc.201800011

M3 - RGC 21 - Publication in refereed journal

SN - 2193-5807

VL - 7

SP - 702

EP - 706

JO - Asian Journal of Organic Chemistry

JF - Asian Journal of Organic Chemistry

IS - 4

ER -

Facile Syntheses, Characterization, and Physical Properties of Sulfur-Decorated Pyran-Annulated Perylene Diimides

Abstract

Research Keywords

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